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Chloroethane → 4-Phenyl-4-propionyloxy-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzyloxycarbonylamino)ethoxy]ethyl]piperidine hydrochloride hemihydrate

HRID 1841
Notes
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Reaction equation

HRID 1841 reaction equation
Cl.[OH:2][C:3]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][CH:12]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH2:13][N:14]([CH3:25])[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:47]([Cl:51])(=[O:50])[CH2:48][CH3:49].CCCl>C(Cl)Cl>[OH2:2].[ClH:32].[C:34]1([C:3]2([O:2][C:47](=[O:50])[CH2:48][CH3:49])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][CH:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:13][N:14]([CH3:25])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:5][CH2:4]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[C:34]1([C:3]2([O:2][C:47](=[O:50])[CH2:48][CH3:49])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][CH:12]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=3)[CH2:13][N:14]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH3:25])[CH2:5][CH2:4]2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1.[ClH:51]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6337ChloroethaneHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 196924894-Hydroxy-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzyloxycarbonylamino)ethoxy]ethyl]piperidine hydrochloride

Product 1

HCID 131720561
4-Phenyl-4-propionyloxy-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzyloxycarbonylamino)ethoxy]ethyl]piperidine hydrochloride hemihydrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

670 mg of the compound obtained in EXAMPLE 9 are dissolved in 10 ml of methylene chloride, and 0.2 ml of triethylamine and 0.2 ml of propionyl chloride are then added, with stirring. After 15 minutes, the reaction mixture is washed with water and then with 10% Na2CO3 solution and the organic phase is dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (97/3; v/v) as the eluent. The product obtained is taken up with DCM, acidified to pH 1 by the addition of hydrochloric ether and concentrated under vacuum to give 0.52 g of the expected hydrochloride after crystallization from pentane. M.p.=115° C. (dec.).

Workup

  1. washthe reaction mixture is washed with water
  2. dry with materialwith 10% Na2CO3 solution and the organic phase is dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue is chromatographed on silica gel H
  5. customThe product obtained
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1ef8b43a3b744c0190064171c4bf7822
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726313

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes