Hydrochloric Acid → 2-(Piperidin-4-yl)benzonitrile hydrochloride

HRID 1250696Notes

Reaction equation

HRID 1250696 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:22]>C(OCC)(=O)C>[ClH:22].[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18326585Tert-butyl 4-(2-cyanophenyl)piperidine-1-carboxylate

Product 1

HCID 183266272-(Piperidin-4-yl)benzonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1-tertbutoxycarbonylpiperidin-4-yl)benzonitrile (1.7 g, 5.9 mmol) in ethyl acetate (˜50 ml), cooled to 0° C. was added hydrogen chloride gas, bubbled vigorously for 5 minutes. The reaction mixture was stirred for 10 minutes at 0° C., purged with argon and concentrated. Flushing with ethyl acetate×3 and concentration gave 2-(piperidin-4-yl)benzonitrile hydrochloride; 1H NMR (DMSO) d 1.98 (m, 4H), 3.07 (m, 2H), 3.21 (tt, 1H, J=12 Hz, J=3.8 Hz), 3.36 (m, 2H), 7.46 (m, 2H), 7.74 (bt, 1H, J=7.7 Hz), 7.83 (bd, 1H, J=7.0 Hz), 9.10 (bd, 2H).

Workup

  1. custombubbled vigorously for 5 minutes
  2. custompurged with argon
  3. concentrationconcentrated
  4. customFlushing with ethyl acetate×3 and concentration

Sources & evidence

ORD record
ord-1159d0227e77412097d8811419e58a05
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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