Dichloromethane → n-(4-Chlorophenyl)({1-[(4-(2-pyridyloxy)phenyl)methyl](4-piperidyl)}[4-(trifluoromethyl)phenyl]methoxy)carboxamide

HRID 1594340Notes

Reaction equation

HRID 1594340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.C(Cl)Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([CH:34]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)[OH:35])[CH2:30][CH2:29]2)=[CH:23][CH:22]=1>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([O:35][CH:34]([CH:31]2[CH2:32][CH2:33][N:28]([CH2:27][C:24]3[CH:25]=[CH:26][C:21]([O:20][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=4)=[CH:22][CH:23]=3)[CH2:29][CH2:30]2)[C:36]2[CH:37]=[CH:38][C:39]([C:42]([F:44])([F:45])[F:43])=[CH:40][CH:41]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 76934-Chlorophenyl IsocyanateHCID 11554030{1-[(4-(2-Pyridyloxy)phenyl)methyl](4-piperidyl)}[4-(trifluoromethyl)phenyl]methanol

Product 1

HCID 11671587n-(4-Chlorophenyl)({1-[(4-(2-pyridyloxy)phenyl)methyl](4-piperidyl)}[4-(trifluoromethyl)phenyl]methoxy)carboxamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
35 °C

Procedure

A 0.06 gram (0.0004 mole) sample of 4-chlorophenylisocyanate was weighed into a two-dram vial, followed in turn by 1.2 mL of methylene chloride, 0.18 gram (0.0004 mole) of {1-[(4-(2-pyridyloxy)phenyl)methyl](4-piperidyl)}[4-(trifluoromethyl)phenyl]methanol, and 0.06 mL of triethylamine. The vial was tightly capped and gently shaken at 35° C. for 16 hours using a vortex mixer. After this time, the methylene chloride was removed under a nitrogen stream to provide a residue. The residue was purified with column chromatography on silica gel using mixtures of acetone and methylene chloride as eluants. The appropriate fractions were combined and concentrated under reduced pressure, yielding 0.2 gram of Compound 227. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThe vial was tightly capped
  2. customAfter this time, the methylene chloride was removed under a nitrogen stream
  3. customto provide a residue
  4. customThe residue was purified with column chromatography on silica gel using mixtures of acetone and methylene chloride as eluants
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-782d76a06fbb471386f1972ca5f33856
Source dataset
uspto-grants-2007_11
Patent number
US07300946B2

Reaction notes

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