Benzaldehyde → HCID 23333353, compound

HRID 224490Notes

Reaction equation

HRID 224490 reaction equation
[CH:1](=[O:8])[C:2]1C=CC=C[CH:3]=1.[CH2:9]([NH:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][N:19]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:35]([O-:40])(=[O:39])[C:36]([O-:38])=[O:37]>>[C:35]([OH:40])(=[O:39])[C:36]([OH:38])=[O:37].[CH2:28]([N:19]1[CH2:20][CH2:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]1[CH2:17][N:16]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:1](=[O:8])[CH2:2][CH3:3])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 71081OxalateHCID 23333328HCID 23333328, compound

Product 1

HCID 23333353HCID 23333353, compound

Procedure

Title Compound I, in which R=CH2C6H5 ; R'=H; A=CH; pY=C2H2O4, q=0 and n=1, was prepared by reducing 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide (6.7 g; 0.025 mole) with LiAlH4 by the same procedure as used in Example I to obtain 3.77 g (60% theory) of 1-aminomethyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline as a yellow oil. This compound was reacted with benzaldehyde and reduced as in Example II. The resultant 1-(N-benzyl)aminomethyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline was propionylated as in Example I and the oxalate (having a melting range of 159°-61°) formed.

Workup

  1. customformed

Sources & evidence

ORD record
ord-b5477947de7e4fb3a6f0b78be6b9055c
Source dataset
uspto-grants-1980_11
Patent number
US04232160

Reaction notes

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