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

HRID 609737Notes

Reaction equation

HRID 609737 reaction equation
N[CH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:4][CH2:3]1.NC1CCC(C2C=C3C(=CC=2)NC=C3CCN2CCCC2)(O)CC1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl.C1COCC1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:5]1([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:17][CH2:18][N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:6][CH2:7][CH2:2][CH2:3][CH:4]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 699483875-(1-aza-1-methyl-4-hydroxycyclohex-4-yl)-3-(2-pyrrolidinylethyl)-1H-indoleHCID 699493865-(1-Aza-1-methylcyclohex-3-en-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole

Product 1

HCID 699489945-(cyclohex-1-en-1-yl)-3-(2-pyrrolidinylethyl)-1H-indole

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(1-Aza-1-methylcyclohex-3-en-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole: (17.6 mg, 13%) from 5-(1-aza-1-methyl-4-hydroxycyclohex-4-yl)-3-(2-pyrrolidinylethyl)-1H-indole (Example 13d, 145 mg, 0.44 mmol), triethylamine (0.95 mL, 6.8 mmol) and MsCl (0.25 mL, 3.2 mmol) in dichloromethane (3.5 mL) and THF (7 mL) with the exception that the reaction was carried out at a gentle reflux overnight and the extraction solvent consisted of a mixture of dichloromethane, chloroform, and ethyl acetate. Starting material (17 mg) was also recovered. The product in this case was converted to the hydrochloride salt which was soluble in methanol; HRMS-FAB+ for C20H27N3 : calculated MH+ :310.22833; found MH+ :310.22650.

Workup

  1. temperaturea gentle reflux overnight
  2. customStarting material (17 mg) was also recovered

Sources & evidence

ORD record
ord-4b3470229f6b48aea2f2e470c5a51fd0
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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