Triethylamine → 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

HRID 609736Notes

Reaction equation

HRID 609736 reaction equation
CS(Cl)(=O)=O.O[C:7]1([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>ClCCl>[NH3:18].[C:7]1([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[C:16]3[CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 699487065-(1-hydroxycyclohex-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

Product 2

HCID 222AmmoniaYield 5%HCID 699489945-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indoleYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.042 mL, 0.54 mmol) was added to a solution of 5-(1-hydroxycyclohex-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 13a, 50.6 mg, 0.16 mmol) and triethylamine (0.15 mL, 1.06 mmol) in dichloromethane (2.5 mL) at 0° C. The reaction was allowed to warm slowly to room temperature and stirring was continued overnight. The reaction mixture was diluted with dichloromethane (100 mL) and washed sequentially with water and brine, dried over sodium sulfate and the solvent was removed in vacuo. Flash chromatography (silica, 5-8% 2M methanolic ammonia in dichloromethane) yielded 5-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole (21.8 mg, 46%); HRMS-FAB+ for C20H26N2 :calculated MH+ :295.21744; found MH+ :295.21953.

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialdried over sodium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1ef81c29f2d24351ac8876be0312f581
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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