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

HRID 2220694

Reaction equation

HRID 2220694 reaction equation
[S:1]1[C:5]([CH:6]=O)=[CH:4][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[C:5]([CH2:6][NH:20][CH2:19][CH2:18][CH:14]2[CH2:15][CH2:16][CH2:17][N:13]2[CH3:12])=[CH:4][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 7365001-Benzothiophene-2-carbaldehydeHCID 5360545Sodium

Product 1

HCID 59773016Benzo[b]thiophen-2-ylmethyl-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-amineYield 26.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Experimental condition analogous to Example 5, from benzo[b]thiophen-2-carbaldehyde 0.18 g (1.1 mmol), 2-(1-methyl-pyrrolidin-2-yl)-ethylamine 0.14 g (1 mmol), and sodium triacethoxyborohydride 0.31 g (1.5 mmol), in 10 mL dichloromethane. Purification using silica gel chromatography, elution with dichloromethane-methanol-ammonium hydroxide, 9-1-0.25, gave 73 mg of compound.

Workup

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

Sources & evidence

ORD record
ord-55cb64f102f44df5b64077a5229a6568
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Linked notes

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