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

HRID 1077367Notes

Reaction equation

HRID 1077367 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, on 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, on oil
  2. filtrationThe resulting solids were filtered
  3. customto give
  4. customafter recrystallization from aqueous ethyl alcohol, 20.5 g

Sources & evidence

ORD record
ord-0a6fb53bac554c8a8de30cffa620ca6a
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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