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

HRID 128128Notes

Reaction equation

HRID 128128 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-7f49660337a34e2d86878c48048d3590
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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