Dimethylformamide → HCID 12891848, compound

HRID 1077340Notes

Reaction equation

HRID 1077340 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 recrystallizaton from isopropyl alcohol - ether 5.6 g. of 3-benzoyloxy-9-[2-(dimethylaino)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 after recrystallizaton from isopropyl alcohol - ether 5.6 g

Sources & evidence

ORD record
ord-8e7680b152374e8a83cee160f89ff4d2
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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