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Benzyl chloroformate → Benzyl 4-(2-hydroxy-4-methoxybenzoyl)piperidine-1-carboxylate

HRID 370883
Notes
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Reaction equation

HRID 370883 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].C(=O)(O)[O-].[Na+].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>ClCCl>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:10][CH2:11]1)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 13076390(2-Hydroxy-4-methoxyphenyl)(piperidin-4-yl)methanone

Product 1

HCID 13076396Benzyl 4-(2-hydroxy-4-methoxybenzoyl)piperidine-1-carboxylateYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, ice-cooled mixture of 36.1 g of 4-(2-hydroxy-4-methoxybenzoyl)piperidine, 16.3 g of sodium bicarbonate and 350 ml of dichloromethane, was added dropwise 22.9 ml of benzyl chloroformate in dichloromethane. After the addition was complete, the mixture was stirred at ambient temperature for 1.5 hrs, filtered and the filtrate concentrated to an oil. The oil crystallized. The crystals were collected, washed with hexane and dried to yield 42.4 g (76.5%) of product. Recrystallization from isopropanol gave the analytical sample, mp, 89°-91°.

Workup

  1. temperatureTo a stirred, ice-cooled
  2. additionAfter the addition
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated to an oil
  5. customThe oil crystallized
  6. customThe crystals were collected
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-835f127002934a9eb25f23cf5570ae03
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04528376

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes