Chloroacetyl chloride → HCID 54401423, compound

HRID 1267918Notes

Reaction equation

HRID 1267918 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([NH2:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[Cl:31][CH2:32][C:33](Cl)=[O:34].C(OCC)(=O)C.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([NH:21][C:33](=[O:34])[CH2:32][Cl:31])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 22728543Water ethylacetateHCID 54324264HCID 54324264, compound

Product 1

HCID 54401423HCID 54401423, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(3-amino-4-chloro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (500 mg) and N,N-diisopropylethylamine (0.8 ml) in tetrahydrofuran (20 ml) cooled to 0° C. was added 2-chloroacetyl chloride (0.2 ml). After 2 hrs, the reaction was poured into ethyl acetate/water. The organic layer was separated, washed with water, aqueous NaHCO3 and brine, dried (MgSO4) and concentrated. Purification of the residue by silica gel chromatography (eluting ethyl acetate/iso-hexane (1:3 to 1:2) gave the sub-title product (0.5 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water, aqueous NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the residue by silica gel chromatography (
  6. washeluting ethyl acetate/iso-hexane (1:3 to 1:2)

Sources & evidence

ORD record
ord-edc834d5531349cd881a3e2648b56bf0
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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