Hydrochloric Acid → HCID 12891849, compound

HRID 128101Notes

Reaction equation

HRID 128101 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+].[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29]Cl.Cl.Cl.C(OC1CC2C3C(=CC=CC=3)NC=2CC1)(=O)C1C=CC=CC=1>CN(C)C=O>[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]([CH2:29][CH2:28][CH2:27][N:26]([CH3:31])[CH3:25])[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 23470342HCID 23470342, compoundHCID 23470368HCID 23470368, compound

Product 1

HCID 12891849HCID 12891849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 3-benzoyloxy-9-[3-(dimethylamino)propyl]-1,2,3,4-tetrahydrocarbazole was prepared by following an alkylation procedure similar to that described in Example 11 and using 29.1 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole and 4.3 g. of sodium hydride (50% in mineral oil) in 200 ml. of dimethylformamide, and 13 g. of 3-(dimethylamino)propyl chloride. The crude free base was extracted from the water diluted reaction mixture into ether and the ethereal solution was treated with ethereal hydrogen chloride. The resulting precipitate was recrystallized from isopropyl alcohol and ethyl acetate to give 6.2 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 162°-180° C.

Workup

  1. extractionThe crude free base was extracted from the water
  2. additiondiluted
  3. customreaction mixture into ether
  4. customThe resulting precipitate was recrystallized from isopropyl alcohol and ethyl acetate
  5. customto give 6.2 g

Sources & evidence

ORD record
ord-e383ea0f98334e979bac20cb8355e499
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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