Water → HCID 54236157, compound

HRID 1578254Notes

Reaction equation

HRID 1578254 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH2:10][CH2:9][CH:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:7][C:6]2=1.[H-].[Na+].[CH3:24][N:25]([CH2:27][CH2:28][CH2:29]Cl)[CH3:26].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:29][CH2:28][CH2:27][N:25]([CH3:26])[CH3:24])[C:11]1[CH2:10][CH2:9][CH:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:7][C:6]2=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 12939676HCID 12939676, compound

Product 1

HCID 54236157HCID 54236157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 6-methoxy-3-phenyl-1,2,3,4-tetrahydrocarbazole (5.5 g), 50% sodium hydride (1.0 g) in dimethylformamide (30 ml) is heated at 100° C. for 11/2 hours, and then dimethylamino propyl chloride is added. The mixture is heated at 80° C. for 2 hours, then cooled and water (40 ml) is added. The solid which precipitates is recrystallized with methylene chloride:ether (1:1).

Workup

  1. temperatureThe mixture is heated at 80° C. for 2 hours
  2. temperaturecooled
  3. customThe solid which precipitates
  4. customis recrystallized with methylene chloride:ether (1:1)

Sources & evidence

ORD record
ord-3b6134ad73e6451baef3a435fef955b1
Source dataset
uspto-grants-1981_09
Patent number
US04292323

Reaction notes

Loading…