Bromoacetyl bromide → (S)-N-{1-[4-(1-(2-Bromoacetyl)piperidin-4-yl)-phenyl]-ethyl}-acetamide

HRID 1470742Notes

Reaction equation

HRID 1470742 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1>ClCCl>[Br:1][CH2:2][C:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 67125412(S)-N-[1-(4-piperidin-4-yl-phenyl)ethyl]-acetamide

Product 1

HCID 67971049(S)-N-{1-[4-(1-(2-Bromoacetyl)piperidin-4-yl)-phenyl]-ethyl}-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

530 μl (6.09 mmol) Bromoacetylbromide are added dropwise to an ice cold mixture of 1.50 g (6.09 mmol) (S)—N-[1-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (V.1) and 1.03 mL (7.31 mmol) TEA in 20 mL dichloromethane. Then the cooling is removed and the mixture is allowed to warm to rt and then quenched by the addition of water. The mixture is extracted with DCM, the org. layers are combined, washed with water and dried with MgSO4. The solvent is removed in vacuo and the crude product is used without further purification.

Workup

  1. customThen the cooling is removed
  2. customquenched by the addition of water
  3. extractionThe mixture is extracted with DCM
  4. washwashed with water
  5. dry with materialdried with MgSO4
  6. customThe solvent is removed in vacuo
  7. customthe crude product is used without further purification

Sources & evidence

ORD record
ord-44ce855b838043ac80fee128773f79db
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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