Triethylamine → 5-(4-acetylphenyl)-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]valeramide

HRID 1241898Notes

Reaction equation

HRID 1241898 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.Cl.[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:22][CH2:21]1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>ClCCl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=3)[CH2:22][CH2:21]2)=[O:16])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219371095-(4-Acetylphenyl)valeric acidHCID 219371291-(3,4-Dichlorobenzyl)piperidin-4-ylamine dihydrochloride

Product 1

HCID 102265315-(4-acetylphenyl)-N-[1-(3,4-dichlorobenzyl)piperidin-4-yl]valeramideYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Acetylphenyl)valeric acid (996 mg) and 4-amino-1-(3,4-dichlorobenzyl)piperidine dihydrochloride (1.50 g) were suspended in dichloromethane (40 mL), and triethylamine (1.26 mL) and EDC hydrochloride (953 mg) were added to the suspension. The suspension was stirred for 12 hrs. The reaction mixture was washed with water and then saturated brine and dried, and the solvent was evaporated under reduced pressure. Diethyl ether was added to the residue to crystallize to give the title compound (1.16 g) as a white solid.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialsaturated brine and dried
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiethyl ether was added to the residue
  5. customto crystallize

Sources & evidence

ORD record
ord-9835a220bb114b1aaf88c848ab885bc4
Source dataset
uspto-grants-2006_10
Patent number
US07115635B2

Reaction notes

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