[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]acetonitrile → Ammonia

HRID 1866543Notes

Reaction equation

HRID 1866543 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>N.[Ni]>[NH3:1].[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 2

HCID 23091635[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]acetonitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 222AmmoniaHCID 549610062-[4-(3-Pyrrolidin-1-yl-propoxy)-phenyl]-ethylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of [4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-acetonitrile (preparation 104), (1 g, 4.1 mmol) and Raney® nickel (100 mg) in 2M methanolic ammonia (35 mL) was stirred under 60 psi of hydrogen gas at 50° C. for 6 hours. Tlc analysis showed that not all of the starting material had been consumed and so further Raney® nickel (200 mg) was added to the reaction mixture and heating continued for 5 hours. Tlc analysis again showed that starting material was still present and so additional Raney® nickel (200 mg) was added and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was then filtered through Arbocel® and was concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography using a 4 g RediSep® silica cartridge, eluting with dichloromethane:methanol:0.88 ammonia, 85:15:1.5 to 80:20:2, to afford the title compound in 16% yield, 160 mg.

Workup

  1. customhad been consumed
  2. additionso further Raney® nickel (200 mg) was added to the reaction mixture
  3. temperatureheating
  4. additionso additional Raney® nickel (200 mg) was added
  5. filtrationThe reaction mixture was then filtered through Arbocel®
  6. concentrationwas concentrated in vacuo
  7. customto give a yellow oil
  8. customThe oil was purified by column chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-090a0a904a2c4707a2688f6e91d8cd3b
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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