6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline synthesis

10synthesis methods

Product Name:6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
CAS Number:54893-54-8
Molecular formula:C11H15NO
Molecular Weight:177.24

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42923-77-3 Synthesis

6-METHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE

42923-77-3
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$21.00/100mg

6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

54893-54-8
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Yield:54893-54-8 260 g

Reaction Conditions:

Stage #1: formalin;6-methoxy-1,2,3,4-tetrahydro-isoquinoline in methanol at 0; for 0.25 h;Inert atmosphere;
Stage #2: with sodium tetrahydridoborate in methanol at 0; for 3 h;Inert atmosphere;

Steps:

3 Step 3.

A 5-L 4-necked round-bottom flask was charged with 6-methoxy-1,2,3,4- tetrahydroisoquinoline (370 g, 2.27 mol), MeOH (4.0 L) and formaldehyde (1.1 L) was added slowly at 0 ^oC. The resulting solution was stirred for 15 min, then NaBH₄ (300 g, 7.93 mol) was added in portions at 0 ^oC. The resulting solution was stirred for 3 h, and quenched with water (1 L). The resulting mixture was stirred for 30 min, then concentrated under reduced pressure. The resulting mixture was diluted with water (5 L) and extracted with DCM (3 x 3 L). The combined organic layers were concentrated in vacuo, giving 6-methoxy-2-methyl- 1,2,3,4-tetrahydroisoquinoline (260 g).

References:

WO2022/98809,2022,A1 Location in patent:Page/Page column 51; 54-55

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57196-62-0 Synthesis