Ammonia → HCID 21477559, compound

HRID 2293646Notes

Reaction equation

HRID 2293646 reaction equation
[ClH:1].[CH2:2]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C:18]#[N:19])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N>C(O)C.O.[Ni]>[ClH:26].[ClH:1].[NH2:19][CH2:18][CH:17]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)[CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][CH2:11]1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 21477588HCID 21477588, compound

Product 1

HCID 21477559HCID 21477559, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

14.5 g of 4-(4-benzylpiperidin-1-yl)-2-(3,4-dichlorophenyl)butyronitrile hydrochloride are dissolved in 400 ml of 95° ethanol. A solution of 20 ml of concentrated ammonia in 40 ml of water and Raney nickel (10% by weight of the amount of amine) are added to the mixture, which is then placed under a hydrogen atmosphere, with vigorous stirring, for 4 hours, after which 1.67 l of hydrogen have been consumed. After filtration of the catalyst, the filtrate is concentrated under vacuum and the residue is taken up in ethyl acetate, washed with water, dried and concentrated under vacuum. The residue is taken up in a solution of hydrogen chloride in methanol, filtered off and recrystallized from a 3/7 acetone/ether mixture.

Workup

  1. customafter which 1.67 l of hydrogen have been consumed
  2. filtrationAfter filtration of the catalyst
  3. concentrationthe filtrate is concentrated under vacuum
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under vacuum
  7. filtrationfiltered off
  8. customrecrystallized from a 3/7 acetone/ether mixture

Sources & evidence

ORD record
ord-359cbf5cc26f4abf8ee503371283263a
Source dataset
uspto-grants-1997_11
Patent number
US05686609

Reaction notes

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