Oxalic Acid → (2-Benzyl-1,2,3,4-tetrahydroisoquinolin-1-YL)methanamine

HRID 224489Notes

Reaction equation

HRID 224489 reaction equation
O=C(C(=O)O)O.[CH2:7]([N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]1[C:24]([NH2:26])=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[NH2:26][CH2:24][CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][N:14]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 971Oxalic AcidHCID 21226445Aluminium lithium hydrideHCID 233333632-Benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide

Product 1

HCID 12857708(2-Benzyl-1,2,3,4-tetrahydroisoquinolin-1-YL)methanamineYield 60%

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.

Sources & evidence

ORD record
ord-72a26f61064146bf852600a44d728f83
Source dataset
uspto-grants-1980_11
Patent number
US04232160

Reaction notes

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