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Dimethylamine, hydrate → [3-(4-Chloro-pyridin-2-yl)-thiophen-2-ylmethyl]-dimethyl-amine

HRID 910697
Notes
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Reaction equation

HRID 910697 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH:13]=O)[CH:3]=1.O.[CH3:16][NH:17][CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:13][N:17]([CH3:18])[CH3:16])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27521Dimethylamine, hydrateHCID 5049666Sodium triacetoxyborohydrideHCID 866286363-(4-Chloro-pyridin-2-yl)-thiophene-2-carbaldehyde

Product 1

HCID 67387695[3-(4-Chloro-pyridin-2-yl)-thiophen-2-ylmethyl]-dimethyl-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-chloro-pyridin-2-yl)-thiophene-2-carbaldehyde (20 mg, 0.1 mmol) in dichloromethane (3 mL) was added dimethylamine water solution (40%, 0.6 mL) and sodium triacetoxyborohydride (42 mg, 0.2 mmol). The resulting mixture was stirred at room temperature for 16 hours, then washed with NaHCO3 solution and water and concentrated. The resulting residue was purified by preparative TLC to yield [3-(4-Chloro-pyridin-2-yl)-thiophen-2-ylmethyl]-dimethyl-amine.

Workup

  1. washwashed with NaHCO3 solution and water
  2. concentrationconcentrated
  3. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-6b068d62dc414041a43940723b74c8c1
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08022209B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes