Water → HCID 13584819, compound

HRID 918340Notes

Reaction equation

HRID 918340 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 1/2 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 1/2 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-e3b412ef422a4eb999bb47ec039aea2e
Source dataset
uspto-grants-1976_07
Patent number
US03970757

Reaction notes

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