Ammonia → HCID 15055868, compound

HRID 1651561

Reaction equation

HRID 1651561 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C1([N:34]=C=NC2CCCCC2)CCCCC1.N>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([NH2:34])=[O:21])[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 23504-((4-Chlorophenyl)-2-pyridinylmethoxy)-1-piperidinebutanoic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 15055868HCID 15055868, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.50 g (1.29 mmol) of 4-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]butanoic acid obtained in Example 28 was dissolved in 5 ml of dichloromethane, and 0.32 g (1.55 mmol) of dicyclohexylcarbodiimide was added to the reaction mixture on an ice bath. Then, 10 ml of ammonia gas dissolved dichloromethane solution was added, and the mixture was stirred at room temperature for 10 hours. After the reaction, the insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using a mixture of chloroform, methanol and conc. ammonia water (conc. 25% by weight) in the volume ratio 90:9:1 as the eluent. The desired fraction was concentrated under reduced pressure to give 0.38 g (76%) of 4-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]butanamide as an oil.

Workup

  1. additionwas added
  2. customAfter the reaction
  3. filtrationthe insolubles were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was separated by silica gel column chromatography
  6. additiona mixture of chloroform, methanol and conc. ammonia water (conc. 25% by weight) in the volume ratio 90:9:1 as the eluent
  7. concentrationThe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a956e29214ce4fe8a8f381c312d770b1
Source dataset
uspto-grants-1990_05
Patent number
US04929618

Linked notes

Loading…