Triethylamine → Trans-(+/-)-N-[2-(1-pyrrolidinyl)cyclohexyl]-N,2,3-trimethyl-1H-indole-5-acetamide

HRID 542216Notes

Reaction equation

HRID 542216 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH3:18])=[CH:15][C:14]([CH2:19][C:20]([OH:22])=O)=[CH:13][CH:12]=2.ClC(OCC)=O.[CH3:29][NH:30][C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]1[N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>O1CCCC1>[N:37]1([C@@H:32]2[CH2:33][CH2:34][CH2:35][CH2:36][C@H:31]2[N:30]([CH3:29])[C:20](=[O:22])[CH2:19][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9]([CH3:8])=[C:17]3[CH3:18])[CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 8262542-(2,3-dimethyl-1H-indol-5-yl)acetic acidHCID 13377463Cyclohexanamine, N-methyl-2-(1-pyrrolidinyl)-, trans-

Product 1

HCID 18607182Trans-(+/-)-N-[2-(1-pyrrolidinyl)cyclohexyl]-N,2,3-trimethyl-1H-indole-5-acetamideYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (139 μl, 1 mmol) was added to a solution of 2,3-dimethyl-1H-indole-5-acetic acid (203 mg, 1 mmol) in tetrahydrofuran (10 ml) at -15° C., with vigorous stirring. Ethyl chloroformate (96 μl, 1 mmol) was added, and the mixture stirred for five minutes. A solution of trans-(±)-N-methyl-2-(1-pyrrolidinyl)cyclohexanamine (182 mg, 1 mmol) in tetrahydrofuran (2 ml) was added, and stirring continued for 30 minutes at -15° C., then 30 minutes at room temperature. The reaction was evaporated to small volume, the residue taken into ethyl acetate (50 ml), and washed with saturated sodium bicarbonate solution (3×50 ml). The organic extract was dried (MgSO4), evaporated under reduced pressure and recrystallized from ethyl acetate to yield the amide (204 mg, 56%); VmaxC=0 1615 cm-1.

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes at -15° C.
  3. custom30 minutes
  4. customat room temperature
  5. customThe reaction was evaporated to small volume
  6. washwashed with saturated sodium bicarbonate solution (3×50 ml)
  7. extractionThe organic extract
  8. dry with materialwas dried (MgSO4)
  9. customevaporated under reduced pressure
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f23bce09ea1a42ffbf91fb2967c89627
Source dataset
uspto-grants-1987_04
Patent number
US04656182

Reaction notes

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