Acetyl bromide → HCID 22993462, compound

HRID 1275232Notes

Reaction equation

HRID 1275232 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][C:18]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:30](Br)(=[O:32])[CH3:31]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][C:18]([O:27][C:30](=[O:32])[CH3:31])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10482Acetyl bromideHCID 24758Sodium hydrideHCID 10619040N-Benzyloxycarbonyl-3-(4-hydroxy-4-phenylpiperidin-1-yl)propylamine

Product 1

HCID 22993462HCID 22993462, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyloxycarbonyl-3-(4-hydroxy-4-phenylpiperidin-1-yl)propylamine (0.5 g, 1.36 mmol) in THF (20 mL) at 0° C., sodium hydride (60% suspension in paraffin, 65 mg, 1.63 mmol, 1.2 eq.) was added and the mixture was stirred for 1.5 h. To this acetyl bromide (0.12 mL, 1.63 mmol) was injected and the mixture was stirred at 0° C. for 30 minutes and at room temperature for 3 h. Solvent was evaporated, the residue was mixed with dichloromethane (100 mL), and washed with water (2×20 mL). Solvent was evaporated from the dried dichloromethane solution gave the product as a viscous oil (0.485 g, 87%). The 1H-NMR showed this product to be pure and was used in the next step without any further purification.

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes and at room temperature for 3 h
  2. customSolvent was evaporated
  3. additionthe residue was mixed with dichloromethane (100 mL)
  4. washwashed with water (2×20 mL)
  5. customSolvent was evaporated from the dried dichloromethane solution

Sources & evidence

ORD record
ord-7e54b2a2cb284df9aa159da593c2cc17
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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