Triethylamine → Methyl 4-{[1-(3,4-dichlorobenzyl)-4-piperidinyl]amino}-4-oxobutanoate

HRID 1070497Notes

Reaction equation

HRID 1070497 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]1.Cl[C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([NH:13][C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 516892Sodium BicarbonateHCID 223962061-(3,4-Dichloro-benzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 22396186Methyl 4-{[1-(3,4-dichlorobenzyl)-4-piperidinyl]amino}-4-oxobutanoateYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3,4-dichlorobenzyl)-4-piperidinamine hydrochloride (3.50 g) in dichloromethane (100 ml) was added methyl 4-chloro-4-oxobutanoate (2.00 g) dropwise. Triethlamine (3.90 g) was added and the reaction stirred under nitrogen for 2 hours. Saturated sodium hydrogen carbonate solution was then added, with the solution being extracted three times with dichloromethane. The pooled organic phase was washed once with water, once with saturated brine and dried over anhydrous magnesium sulfate. After filtration the solvent was removed under reduced pressure to leave methyl 4-{[1-(3,4-dichlorobenzyl)-4-piperidinyl]amino}-4-oxobutanoate (3.00 g).

Workup

  1. extractionbeing extracted three times with dichloromethane
  2. washThe pooled organic phase was washed once with water, once with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration the solvent
  5. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-8d5f1eea97bc47f98bbd7a892febd140
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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