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

HRID 542214Notes

Reaction equation

HRID 542214 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([OH:13])=O)=[CH:2]1.[CH3:14][NH:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C1(N=C=N)CCCCC1>O1CCCC1>[CH3:14][N:15]([C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:11](=[O:13])[CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 802Indole-3-Acetic AcidHCID 12048208N-CyclohexylcarbodiimideHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

Product 1

HCID 14040447trans-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexyl]-1H-indole-3-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1H-Indole 3-acetic acid (1.05 g, Aldrich) and trans-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine were dissolved in tetrahydrofuran (30 ml) and cyclohexyl carbodiimide (1.24 g) added. The resultant solution was stirred at room temperature overnight, during which time a white precipitate appeared. The solution was filtered and evaporated to an oil, which was chromatographed on silica. Elution with ether gave the product as a white solid (1.3 g), mp 175°-178° C.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated to an oil, which
  3. customwas chromatographed on silica
  4. washElution with ether

Sources & evidence

ORD record
ord-0dff0373840845128d60a335a7648e29
Source dataset
uspto-grants-1987_04
Patent number
US04656182

Reaction notes

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