Triethylamine → HCID 18318117, compound

HRID 2256043Notes

Reaction equation

HRID 2256043 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].CO.ClCCl>ClCCl.C(Cl)(Cl)Cl>[CH2:25]([O:24][C:22]([N:5]1[CH2:6][CH2:7][C:2]([OH:1])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:4]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 963874-Phenylpiperidin-4-olHCID 21226129Dichloromethane methanol

Product 1

HCID 18318117HCID 18318117, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-6 °C

Procedure

A suspension of 4-hydroxy-4-phenylpiperidine (10 g) in dichloromethane (90 mL) was treated with triethylamine (5.71 g) and cooled to -6° C. This reaction mixture was treated with benzyl chloroformate (9.62 g) in 1 mL portions, stirred for 3 hours and diluted with chloroform (100 mL), washed with 1N HCl, and extracted with chloroform. The organic layers were washed with brine, dried and evaporated to afford the crude material. Chromatography, with methanol:dichloromethane (1:30) as the eluent, gave the benzyloxycarbonylpiperidine (9.4 g); MS: m/z=312(M+1); NMR: 1.6 (d, 2, J=10), 1.77-1.89 (m, 2), 3.91 (m, 2), 5.09 (s,2), 7.18-7.48 (m, 10).

Workup

  1. washwashed with 1N HCl
  2. extractionextracted with chloroform
  3. washThe organic layers were washed with brine
  4. customdried
  5. customevaporated
  6. customto afford the crude material

Sources & evidence

ORD record
ord-68bda02f3df9418882f1a075484eae17
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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