Acetyl chloride → HCID 57656745, compound

HRID 2371209Notes

Reaction equation

HRID 2371209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C@H:20]3[CH2:25][N:24]([CH2:26][CH3:27])[CH2:23][CH2:22][NH:21]3)=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:35](Cl)(=[O:37])[CH3:36]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:35]([N:21]1[CH2:22][CH2:23][N:24]([CH2:26][CH3:27])[CH2:25][C@@H:20]1[C:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[O:11])[CH2:17][CH2:16]1)=[O:19])(=[O:37])[CH3:36]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57656871HCID 57656871, compound

Product 1

HCID 57656745HCID 57656745, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-(3,4-Dichlorophenyl)-4-{[(2R)-4-ethylpiperazin-2-yl]carbonyl}piperazine-1-carboxamide (70 mg) in chloroform (1 ml) was cooled in an ice bath, triethylamine (19 ul) added, followed by acetyl chloride (10 ul) and the mixture stirred for 2 hours at 0° C. The mixture was diluted with CH2Cl2, washed with saturated aqueous sodium bicarbonate, the organic phase dried (MgSO4), evaporated and the residue purified on a 4 g Redisep® SiO2 column, eluting with 0-50% MeOH/CH2Cl2 to give the title compound as a colourless solid (35 mg, 45%).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialthe organic phase dried (MgSO4)
  3. customevaporated
  4. customthe residue purified on a 4 g Redisep® SiO2 column
  5. washeluting with 0-50% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d248538995d542d3aab131cfabf89ad8
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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