1H-Indole-3-propanamide, N-methyl- → HCID 21472501, compound

HRID 1702923Notes

Reaction equation

HRID 1702923 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([NH:14][CH3:15])=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:15][NH:14][CH2:12][CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 76616991H-Indole-3-propanamide, N-methyl-HCID 21226445Aluminium lithium hydride

Product 1

HCID 21472501HCID 21472501, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 60.6 g 3-(3-indolyl)-N-methyl-propionamide in 500 ml anhydrous tetrahydrofuran are added dropwise at 25° for 15 minutes under nitrogen atmosphere to a suspension of 34.2 g lithium aluminium hydride in 800 ml anhydrous tetrahydrofuran and maintained at 66° for 3 hours. N-methyl-3-(3-indolyl)-propylamine (M.pt 81°-82° after crystallization from methylene chloride/ethyl acetate) is obtained after working up.

Workup

  1. temperaturemaintained at 66° for 3 hours

Sources & evidence

ORD record
ord-32347f998b68432dbcbb537f83dfde11
Source dataset
uspto-grants-1982_09
Patent number
US04350634

Reaction notes

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