Water → HCID 18672412, compound

HRID 1058240Notes

Reaction equation

HRID 1058240 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:16][N:17]2[CH2:20][C:19]([F:22])([F:21])[CH2:18]2)=[C:12]([CH:15]=1)[C:13]#[N:14].O.[OH-].[Na+]>CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:16][N:17]2[CH2:18][C:19]([F:22])([F:21])[CH2:20]2)=[C:12]([CH:15]=1)[CH2:13][NH2:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18672418HCID 18672418, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18672412HCID 18672412, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1M LAH in ether (0.42 mL, 0.42 mmol) was added to a stirred solution of 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzonitrile (67.8 mg, 0.28 mmol) in ether (5 ml) at 0° C. After 1 h the reaction was treated successively with water (16 μL), 15% NaOH (16 μL), and water (32 μL). After stirring for 15 min the mixture was filtered and the filtrate was evaporated. The residue was partitioned between 1N HCl and ether. The aqueous layer was made neutral with NaHCO3 and was extracted with CH2Cl2. The organic layer was dried with Na2SO4 and evaporated to give 5-chloro-2-[(3,3-difluoroazetidin-1-yl)methyl]benzylamine (61 mg) as a glass: 1H NMR (CDCl3, 400 MHz) δ 3.56 (t, J=11.9 Hz, 4H), 3.73 (s, 2H), 3.85 (s, 2H), 7.26 (m, 3H).

Workup

  1. filtrationwas filtered
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between 1N HCl and ether
  4. extractionwas extracted with CH2Cl2
  5. dry with materialThe organic layer was dried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-030a77750ffc479eb68cb441b9f32ae9
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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