Hydrochloric Acid → 3-Chloro-N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}benzamide hydrochloride

HRID 496875Notes

Reaction equation

HRID 496875 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][C:24]=1[Cl:25])[O:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C.[Cl:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39](Cl)=[O:40].Cl>CN(C=O)C.CCOCC.C(OCC)(=O)C.O>[ClH:8].[Cl:35][C:36]1[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=1)[C:39]([NH:21][CH2:20][CH2:19][N:16]1[CH2:15][CH2:14][CH:13]([O:12][C:11]2[CH:22]=[CH:23][C:24]([Cl:25])=[C:9]([Cl:8])[CH:10]=2)[CH2:18][CH2:17]1)=[O:40]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 69252Benzoyl chloride, 3-chloro-HCID 81531DiisopropylethylamineHCID 223224532-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]ethylamine trifluoroacetate

Product 1

HCID 223224173-Chloro-N-{2-[4-(3,4-dichlorophenoxy)-1-piperidinyl]ethyl}benzamide hydrochloride

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 1 step (iv) (0.15 g) was dissolved in DMF (3 ml), N,N-di-isopropylethylamine (0.3 ml) and 3-chlorobenzoyl chloride (0.054 ml) were added. After 2 hours at room temperature, water and ethyl acetate were added, the organic phase separated dried and concentrated. The residue was purified by chromatography (dichloromethane:methanol, 95:5) to give an oil which was dissolved in ether and 1.0M ethereal hydrogen chloride solution added to give the titled product as a solid (0.12 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (dichloromethane:methanol, 95:5)
  5. customto give an oil which

Sources & evidence

ORD record
ord-ecd1b6b9e94d4e03b8f27da1b58bd8a2
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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