Pyridine → HCID 59527751, compound

HRID 2189988Notes

Reaction equation

HRID 2189988 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.N1C=CC=CC=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29]([C:31]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])[CH3:27])=[CH:22][CH:21]=1.[Na+].[Cl-]>ClCCl>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29]([C:31]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:32][CH2:33][N:34]([C:7]([Cl:10])=[O:6])[CH2:35][CH2:36]2)=[O:30])[CH3:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 94429TriphosgeneHCID 86646238HCID 86646238, compound

Product 1

HCID 59527751HCID 59527751, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of triphosgene (172 mg, 0.6 mmol) in dichloromethane (6 mL) at 0° C. under an argon atmosphere was added a solution of pyridine (106 μL, 1.32 mmol) in dichloromethane (3 mL) and a solution of 4-phenyl-piperidine-4-carboxylic acid [(S)-1-(4-fluoro-phenyl)-ethyl]-amide (195 mg, 0.6 mmol) in dichloromethane (6 ml). After stirring at room temperature for 12 h the reaction mixture was poured into ice water, the aqueous layer was saturated with NaCl, then extracted 6 times with dichloromethane, the combined organic layers were dried over Na2SO4 and the solvents were evaporated. The residue was purified by flash chromatography over a 10 g silica gel column with n-heptane and ethyl acetate to yield 233 mg 4-[(S)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-4-phenyl-piperidine-1-carbonyl chloride. MS ISN (m/e): 387.4 [(M−H)−].

Workup

  1. extractionextracted 6 times with dichloromethane
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. customthe solvents were evaporated
  4. customThe residue was purified by flash chromatography over a 10 g silica gel column with n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-fb6d736062ca440280eba4ee022c9d6f
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

Loading…