Water → HCID 59442638, compound

HRID 657501Notes

Reaction equation

HRID 657501 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([O:22][CH2:23][CH:24]3[CH2:26][CH2:25]3)[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#N)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-:27].[K+].[OH2:29].S([O-])(O)(=O)=O.[Na+]>C(O)CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([O:22][CH2:23][CH:24]3[CH2:26][CH2:25]3)[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]([OH:29])=[O:27])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 516919Sodium BisulfateHCID 59442685HCID 59442685, compound

Product 1

HCID 59442638HCID 59442638, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
195 °C

Procedure

2.3 g of 4-(3-bromophenyl)-4-cyclopropylmethoxy-1-phenylcyclohexanecarbonitrile were suspended in 10 ml of ethylene glycol, 0.94 g of potassium hydroxide was added and the mixture was heated for 4 h at 195° C. The reaction mixture was then allowed to stand for 16 h at room temperature, poured onto 100 ml of water and adjusted to pH=3 with saturated aqueous sodium hydrogensulfate solution. The precipitated product was filtered off with suction and purified by preparative HPLC (column: Waters X-Terra MS C18 prep, 200×50 mm, 10 μm; eluent A: water+0.2% TFA, eluent B: acetonitrile; gradient and flow: 90% A+10% B and 50 ml/min for 2.2 min, then to 90% A+10% B and 150 ml/min in 1.3 min, then 90% A+10% B and 150 ml/min for 0.5 min, then to 80% A+20% B and 150 ml/min in 0.5 min, then to 5% A+95% B and 150 ml/min in 19.5 min, then 5% A+95% B and 150 ml/min for 6 min, then to 90% A+10% B and 150 ml/min in 1 min, then 90% A+10% B and 150 ml/min for 4 min). 215 mg of the title compound were obtained as a colorless oil.

Workup

  1. filtrationThe precipitated product was filtered off with suction
  2. custompurified by preparative HPLC (column
  3. waitgradient and flow: 90% A+10% B and 50 ml/min for 2.2 min
  4. waitto 90% A+10% B and 150 ml/min in 1.3 min
  5. wait90% A+10% B and 150 ml/min for 0.5 min
  6. waitto 80% A+20% B and 150 ml/min in 0.5 min
  7. waitto 5% A+95% B and 150 ml/min in 19.5 min
  8. wait5% A+95% B and 150 ml/min for 6 min
  9. waitto 90% A+10% B and 150 ml/min in 1 min
  10. wait90% A+10% B and 150 ml/min for 4 min)

Sources & evidence

ORD record
ord-4b5afffda9fa421a812da4ee6ec2ffbe
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

Loading…