Hydrochloric Acid → Ethyl 3-(dimethylamino)-1,2,3,4-tetrahydrocarbazole-9-propionate

HRID 461568Notes

Reaction equation

HRID 461568 reaction equation
[CH3:1][N:2]([CH3:16])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.Cl>CO.C(O)C.C1C=CC=CC=1>[CH3:1][N:2]([CH3:16])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH2:19][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=2[CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 36082CyclindoleHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 12361849Ethyl 3-(dimethylamino)-1,2,3,4-tetrahydrocarbazole-9-propionate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 256 and using 20 g. of 3-(dimethylamino)-1,2,3,4-tetrahydrocarbazole, 20 g. of ethyl acrylate, 1 ml. of 35% benzyltrimethylammonium hydroxide in methyl alcohol and 150 ml. of benzene and increasing the reflux time to three hours, there was obtained, on the evaporation of the reaction mixture to dryness, an oil, a solution of which in ethyl alcohol was treated with hydrogen chloride in ethyl alcohol. The resulting solids were filtered to give, after recrystallization from aqueous ethyl alcohol, 20.5 g. of ethyl 3-(dimethylamino)-1,2,3,4-tetrahydrocarbazole-9-propionate hydrochloride, m.p. 259°-261° C.

Workup

  1. customthere was obtained, on the evaporation of the reaction mixture to dryness
  2. filtrationThe resulting solids were filtered
  3. customto give
  4. customafter recrystallization from aqueous ethyl alcohol, 20.5 g

Sources & evidence

ORD record
ord-b6ce0d2e358d49ae8063fc229cdc61e9
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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