Indole-3-Acetic Acid → trans-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-3-acetamide monohydrochloride

HRID 542213Notes

Reaction equation

HRID 542213 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH2:23][C:24](O)=[O:25])=[CH:15]1.S(Cl)([Cl:29])=O.CCOCC>C(Cl)Cl>[ClH:29].[CH3:1][N:2]([C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:24](=[O:25])[CH2:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:14][CH:15]=1

Participants

6

Reactant 4

HCID 802Indole-3-Acetic AcidHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

Product 1

HCID 70352298trans-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-1H-indole-3-acetamide monohydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trans-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine (0.368 g) was dissolved in methylene chloride (10 ml) and stirred at room temperature. The acid chloride of 3-indole acetic acid (prepared by the action of thionyl chloride on 3-indole acetic acid, 0.35 g) dissolved in methylene chloride (10 ml) was added and let stand for five hours. Ether was added to rapidly stirred solution until no more precipitate appeared. After further rapid stirring for one hour, the precipitate was filtered and dried in a vacuum oven at 90° C. for one hour and stored in a predried bottle. The product was in the form of a black glassy solid (300 mg).

Workup

  1. additionwas added
  2. stirringAfter further rapid stirring for one hour
  3. filtrationthe precipitate was filtered
  4. customdried in a vacuum oven at 90° C. for one hour

Sources & evidence

ORD record
ord-cbfb82d7941c46abb4d7a72f6132adf3
Source dataset
uspto-grants-1987_04
Patent number
US04656182

Reaction notes

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