Diethyl Malonate → (2-Benzyl-1,2,3,4-tetrahydroisoquinolin-1-YL)methanamine

HRID 1287839Notes

Reaction equation

HRID 1287839 reaction equation
NCC1C2C(=CC=CC=2)CCN1CCCC(OCC)=O.[C:21]([NH:29][CH2:30][CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][N:32]1CCCl)(=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)CC(OCC)=O.C(O[K])CCC>C(O)(C)(C)C>[NH2:32][CH2:33][CH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30][N:29]1[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 21506615HCID 21506615, compoundHCID 215066631-Aminomethyl-2-(3-carbethoxypropyl)-1,2,3,4-tetrahydroisoquinolineHCID 178454393potassium butan-1-olate

Product 1

HCID 12857708(2-Benzyl-1,2,3,4-tetrahydroisoquinolin-1-YL)methanamine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1-aminomethyl-2-(3-carbethoxypropyl)-1,2,3,4-tetrahydroisoquinoline [obtainable by reacting 1-benzamidomethyl-2-(2-chloroethyl)-1,2,3,4-tetrahydroisoquinoline with diethyl malonate in the presence of tert.--C4H9OK in tert.-butanol, saponifying, decarboxylation, and esterification]

Sources & evidence

ORD record
ord-362aadf8c28b4844af62e020a6d8b2e6
Source dataset
uspto-grants-1976_10
Patent number
US03985881

Reaction notes

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