Hydrochloric Acid → 3-[3-[4-(2-Acetoxyethoxy)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride

HRID 50072Notes

Reaction equation

HRID 50072 reaction equation
O.Cl.[C:3]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=2)([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][C:23]([O:32][CH2:33][CH2:34][OH:35])([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)[CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:51](Cl)(=[O:53])[CH3:52].Cl>C(Cl)Cl>[ClH:42].[C:51]([O:35][CH2:34][CH2:33][O:32][C:23]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][CH2:17][C:13]2([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=3)[CH2:14][CH2:15][CH2:16][N:11]([C:3](=[O:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:12]2)[CH2:21][CH2:22]1)(=[O:53])[CH3:52]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 227418231-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(2-hydroxyethoxy)-4-phenylpiperid-1-yl]propyl]piperidine hydrochloride monohydrate

Product 1

HCID 227417883-[3-[4-(2-Acetoxyethoxy)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.6 g of the compound obtained in EXAMPLE 17 and 0.5 ml of triethylamine in 25 ml of DCM is cooled to 0-5° C., 0.085 ml of acetyl chloride is added and the mixture is stirred for 3 hours, the temperature being allowed to rise to RT. It is concentrated under vacuum, the residue is taken up with water and extracted with AcOEt, the organic phase is washed with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM and then a DCM/MeOH mixture (98/2; v/v) as the eluent. The product obtained is dissolved in DCM and acidified by the addition of ethereal hydrogen chloride and the precipitate formed is filtered off to give 1.2 g of the expected product, m.p.=105-107° C.

Workup

  1. customto rise to RT
  2. concentrationIt is concentrated under vacuum
  3. extractionextracted with AcOEt
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica
  8. customThe product obtained
  9. customthe precipitate formed
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-eab46a193f9747f98e682e1e2d8223af
Source dataset
uspto-grants-2004_03
Patent number
US06710042B2

Reaction notes

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