Benzoyl chloride → N-benzoyl-4-hydroxypiperidine

HRID 530480Notes

Reaction equation

HRID 530480 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.N1C=CC=CC=1>[C:9]1([C:8]([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[O:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 79341Piperidin-4-ol

Product 1

HCID 9877704N-benzoyl-4-hydroxypiperidineYield 70.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a four necked round bottom flask, under Argon atmosphere, 4-hydroxypiperidine (5.32 g, 52.6 mmol) was dissolved in CH2Cl2 (28 mL) and pyridine (28 mL). After cooling at 0° C., benzoyl chloride (6.4 mL, 55.2 mmol), dissolved in CH2Cl2 (7 mL) was drop wise added. The ice bath was removed and the mixture stirred 3 h at rt. The solid was filtered-off and the solvent removed under vacuum. Purification by typical column chromatography, eluting with CH2Cl2/MeOH (20:1) afforded the title compound (7.6 g, 70%) as pale yellow oil. Rf=0.21 (CH2Cl2/MeOH 20:1). MS (ESI) m/z: 206 [M−H]+. FTIR (cm−1): 3349, 3065, 3033, 3005, 2934, 2845, 1607, 1574, 1453, 1365, 1339, 1273, 1238, 1180, 1077, 998, 788, 730, 688.

Workup

  1. additionwise added
  2. customThe ice bath was removed
  3. customthe solvent removed under vacuum
  4. customPurification by typical column chromatography
  5. washeluting with CH2Cl2/MeOH (20:1)

Sources & evidence

ORD record
ord-ad6d9a3237064bed87a7ad0419fdff22
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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