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

HRID 2417703Notes

Reaction equation

HRID 2417703 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]

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-683220628e974d8f80deefbf3eb6366a
Source dataset
uspto-grants-1984_09
Patent number
US04469869

Reaction notes

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