Methylamine → 3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine

HRID 1493180Notes

Reaction equation

HRID 1493180 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[O:8][CH2:9][CH2:10][CH2:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)[CH3:3].CN>CCOCC>[NH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 128106112-[3-[3-(N,N-Dimethylaminomethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineYield 79.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-[3-[3-(N,N-Dimethylaminomethyl)phenoxy]propyl]-1H-isoindole-1,3(2H)-dione (25 g) was treated with 30% ethanolic methylamine (150 ml). After 24 hr at room temperature ether (100 ml) was added and a solid was filtered off. The filtrate was distilled to give the title compound as a yellow oil (12.3 g) b.p. 102°-112° (0.2 mm). TLC silica; ethyl acetate:isopropanol:water:0.88 ammonia Rf 0.25.

Workup

  1. filtrationa solid was filtered off
  2. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-61a7d25927b3499b84fba5433fef29a5
Source dataset
uspto-grants-1991_06
Patent number
US05021429

Reaction notes

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