2-(2-Aminoethyl)-1-methylpyrrolidine → Benzo[b]thiophen-3-ylmethyl-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-amine

HRID 2220695Notes

Reaction equation

HRID 2220695 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]=O)[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[CH3:12][N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH2:18][CH2:19][NH2:20].[Na]>ClCCl>[S:1]1[CH:5]=[C:4]([CH2:6][NH:20][CH2:19][CH2:18][CH:14]2[CH2:15][CH2:16][CH2:17][N:13]2[CH3:12])[C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

5

Reactant 3

HCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 2273281-Benzothiophene-3-carbaldehydeHCID 5360545Sodium

Product 1

HCID 59773001Benzo[b]thiophen-3-ylmethyl-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-amineYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental condition analogous to Example 5, from benzo[b]thiophen-3-carbaldehyde 0.16 g (1 mmol), 2-(1-methyl-pyrrolidin-2-yl)-ethylamine 0.14 g (1.1 mmol), and sodium triacethoxyborohydride 0.31 g (1.5 mmol), in 10 mL Dichloromethane. Purification using silica chromatography, elution with dichloromethane-methanol-ammonium hydroxide, 9-1-0.25, gave 140 mg of compound.

Workup

  1. customPurification
  2. washsilica chromatography, elution with dichloromethane-methanol-ammonium hydroxide, 9-1-0.25

Sources & evidence

ORD record
ord-ceeb7ee467ec4b0e9893567dcab2f6a3
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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