Potassium Hydroxide → HCID 58954842, compound

HRID 333227Notes

Reaction equation

HRID 333227 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]#[N:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+]>CC(OC)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][NH2:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 686746441-(3-Chloro-4-fluorophenyl)cyclohexanecarbonitrile

Product 1

HCID 58954842HCID 58954842, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

The title compound was prepared from 1-(3-chloro-4-fluorophenyl)cyclohexanecarbonitrile. A solution of the crude product in MTBE was basicified at 0° C. with KOH, extracted with MTBE and evaporated. The residue was diluted in DCM, filtered through an aminopropyl column and evaporated to give the primary amine (64.1 mg, 25%) as an oil. LCMS Rt=7.62 min, m/z=242 (M+1). 1H NMR (CDCl3, δ) 7.34 (dd, J=2.4, 7.1 Hz, 1H), 7.19 (ddd, J=2.4, 4.6, 8.7 Hz, 1H), 7.11 (t, J=8.7 Hz, 1H), 2.68 (s, 2H), 2.1 (m, 2H), 1.6-1.2 (m, 8H), 0.79 (bs, 2H). 13C NMR (CDCl3, δ, mult): 157.4(0), 154.9(0), 142.2(0), 129.5(0), 127.0(0), 126.9(1), 120.8(1), 120.6(1), 116.3(1), 116.1(1), 54.5(2), 43.3(0), 33.7(2), 26.5(2), 22.0(2).

Workup

  1. extractionextracted with MTBE
  2. customevaporated
  3. additionThe residue was diluted in DCM
  4. filtrationfiltered through an aminopropyl column
  5. customevaporated

Sources & evidence

ORD record
ord-dab1f3f8588b4eed95985ef92d6e48a3
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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