Dimethylformamide → HCID 12891848, compound

HRID 128100Notes

Reaction equation

HRID 128100 reaction equation
[C:1]([O:9][CH:10]1[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CN(C)C=O.[CH3:30][N:31]([CH2:33][CH2:34]Cl)[CH3:32]>C1C=CC=CC=1>[C:1]([O:9][CH:10]1[CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:34][CH2:33][N:31]([CH3:32])[CH3:30])[C:13]=2[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 23470342HCID 23470342, compound

Product 1

HCID 12891848HCID 12891848, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The 3-benzoyloxy-9-[2-(dimethylamino)ethyl]-1,2,3,4-tetrahydrocarbazole was prepared by following an alkylation procedure similar to that described in Example 11 and using 13.1 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole and 1.93 g. of sodium hydride (50% in mineral oil) in 150 ml. of dimethylformamide, and 4.9 g. of (dimethylamino)ethyl chloride in 10 ml. of benzene. An ethereal solution of the crude product was filtered through alumina and the concentrated ethereal eluate was treated with ethereal hydrogen chloride to give after recrystallization from isopropyl alcohol-ether 5.6 g. of 3-benzoyloxy-9-[2-(dimethylamino)ethyl]-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 222°-225° C.

Workup

  1. filtrationAn ethereal solution of the crude product was filtered through alumina
  2. additionthe concentrated ethereal eluate was treated with ethereal hydrogen chloride
  3. customto give
  4. customafter recrystallization from isopropyl alcohol-ether 5.6 g

Sources & evidence

ORD record
ord-0a2f6d44b0a44cf48d61ff85ecd25fd3
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

Loading…