Tert-butyl 4-(3-cyanophenyl)piperidine-1-carboxylate → 3-(Piperidin-4-yl)benzonitrile

HRID 643563Notes

Reaction equation

HRID 643563 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH:12]1[CH2:13][CH2:14][CH:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 59261051Tert-butyl 4-(3-cyanophenyl)piperidine-1-carboxylate

Product 1

HCID 214481663-(Piperidin-4-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 4-(3-cyanophenyl)piperidine-1-carboxylate (376 mg, 1.31 mmol) in 10 mL of 1:1 TFA/DCM was stirred at rt for 1.25 h. The reaction mixture was concentrated. Purification by preparative TLC (silica, 1% of 28% NH4OH solution/9% methanl/UDCM) gave 3-piperidin-4-ylbenzonitrile as a white solid. ESI-MS calc. for C12H14N2: 186; Found: 187 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customPurification by preparative TLC (silica, 1% of 28% NH4OH solution/9% methanl/UDCM)

Sources & evidence

ORD record
ord-00f3cd78edea4c9d8894493927ebb3eb
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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