Hydrochloric Acid → 4-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)

HRID 1487814Notes

Reaction equation

HRID 1487814 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[ClH:22]>C(OCC)(=O)C>[ClH:22].[NH:12]1[CH2:13][CH2:14][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22492960Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate2×

Product 1

HCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)Yield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 500-mL three neck round-bottom flask, was placed a solution of tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate (compound 1.1, 20 g, crude) in ethyl acetate (200 mL). Hydrogen chloride (gas) was introduced to the solution and the resulting mixture was stirred for 30 min at room temperature. The solids were collected by filtration, then washed with ethyl acetate (100 mL) and ether (100 mL) to yield the title compound as a white solid (14 g, 57% over two steps).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with ethyl acetate (100 mL) and ether (100 mL)

Sources & evidence

ORD record
ord-a799ca846b054023849e06efd76ff7ed
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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