4-(1-Cyclobutyl piperidin-4-yloxy)benzonitrile → 4-(1-Cyclobutyl piperidin-4-yloxy)benzylamine

HRID 1523399Notes

Reaction equation

HRID 1523399 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH2:16][NH2:17])=[CH:18][CH:19]=3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 98137774-(1-Cyclobutyl piperidin-4-yloxy)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 682862014-(1-Cyclobutyl piperidin-4-yloxy)benzylamineYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(1-Cyclobutyl piperidin-4-yloxy)benzonitrile (8.22 g, 0.032 moles) in dry tetrahydrofuran (50 mL) was added to a stirred solution of lithium aluminium hydride (3.74 g, 0.098 moles) in dry tetrahydrofuran (30 mL), at 10 to 15° C. under nitrogen atmosphere. The resulting mass was further stirred for 20 minutes at ambient temperature and then refluxed for 4 hours. After completion of reaction, the mass was cooled to 10-15° C., quenched with water and basified with 4N sodium hydroxide solution. Reaction mass was filtered through celite and cake was washed with ethyl acetate. The separated organic layer was dried over sodium sulphate and concentrated under reduced pressure to obtain the title compound 7.17 g (Yield: 86.2%).

Workup

  1. temperaturerefluxed for 4 hours
  2. customAfter completion of reaction
  3. temperaturethe mass was cooled to 10-15° C.
  4. customquenched with water and basified with 4N sodium hydroxide solution
  5. customReaction mass
  6. filtrationwas filtered through celite and cake
  7. washwas washed with ethyl acetate
  8. dry with materialThe separated organic layer was dried over sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-334eb1d327b140d88ec2cb67f4fd67bb
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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