Water → HCID 13584819, compound

HRID 1579511Notes

Reaction equation

HRID 1579511 reaction equation
[H-].[Na+].[C:3]([CH:7]1[CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH2:9][CH2:8]1)([CH3:6])([CH3:5])[CH3:4].[N:20]1([CH2:25][CH2:26]Cl)[CH2:24][CH2:23][CH2:22][CH2:21]1.O>CN(C)C=O>[C:3]([CH:7]1[CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:26][CH2:25][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:10]=2[CH2:9][CH2:8]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 816691-(2-Chloroethyl)pyrrolidineHCID 2588903-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole

Product 1

HCID 13584819HCID 13584819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.20g; 50% dispersion in oil) was added to a solution of 3-tert-butyl-1,2,3,4-tetrahydrocarbazole (5.68g) in dry dimethylformamide (25ml) and the mixture was heated over a steam bath for one-half hour. 2-Pyrrolidinoethyl chloride (3.34g) was then added, and the mixture was heated over the steam bath for a further 4 hours. Thereafter the mixture was cooled at room temperature, allowed to stand for about 16 hours, and poured into water. The aqueous mixture was extracted with diethyl ether, and the ethereal solution was evaporated in vacuo to afford 3-tert-butyl-9-(2-pyrrolidinoethyl)-1,2,3,4-tetrahydrocarbazole as an oil. The latter was distilled under reduced pressure, the principal fraction collected having a b.p. of 185°-195°C/0.05mm. mercury pressure.

Workup

  1. temperaturethe mixture was heated over a steam bath for one-half hour
  2. temperaturethe mixture was heated over the steam bath for a further 4 hours
  3. extractionThe aqueous mixture was extracted with diethyl ether
  4. customthe ethereal solution was evaporated in vacuo

Sources & evidence

ORD record
ord-e284e43fa84a4ab794aa386cf5540e6b
Source dataset
uspto-grants-1976_01
Patent number
US03931222

Reaction notes

Loading…