Hydrochloric Acid → 4-Phenylpiperidine-1-carbonyl chloride

HRID 1942387Notes

Reaction equation

HRID 1942387 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1.[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl>[C:19]1([CH:25]2[CH2:26][CH2:27][N:28]([C:2]([Cl:1])=[O:4])[CH2:29][CH2:30]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 698734-PhenylpiperidineHCID 94429Triphosgene

Product 1

HCID 866513114-Phenylpiperidine-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.68 g (2.26 mmol) triphosgene in 6,8 mL dichloromethane at −80° C. is added 0.52 mL (6.5 mmol) pyridine. Then 1.05 g 4-phenylpiperidine (6.5 mmol) is added over a period of 10 minutes. The reaction mixture is allowed to warm to room temperature and stirred for another 2 hours. 4.5 mL 1N hydrochloric acid is added for hydrolization. The organic phase is separated, washed with saturated sodium bicarbonate solution and dried with sodium sulfate. After evaporation of the solvent the crude product is purified via column chromatography on silica gel using dichloromethane as eluent

Workup

  1. customThe organic phase is separated
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried with sodium sulfate
  4. customAfter evaporation of the solvent the crude product
  5. customis purified via column chromatography on silica gel

Sources & evidence

ORD record
ord-8f59d6352d3c4c15a02a4db48874db0b
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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