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

HRID 1842
Notes
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Reaction equation

HRID 1842 reaction equation
C(N(CC)CC)C.Cl.Cl.[C:10]([NH:13][C:14]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][CH:23]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:24][NH:25][CH3:26])[CH2:16][CH2:15]1)(=[O:12])[CH3:11].Cl[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43].CCCl>C(Cl)Cl>[ClH:33].[C:10]([NH:13][C:14]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][O:22][CH:23]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:24][N:25]([CH3:26])[C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[CH2:18][CH2:19]1)(=[O:12])[CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6337ChloroethaneHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 196925004-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methylamino)ethoxy]ethyl]piperidine dihydrochloride

Product 1

HCID 196924624-Acetamido-4-phenyl-1-[2-[1-(3,4-dichlorophenyl)-2-(N-methyl-N-benzyloxycarbonylamino)ethoxy]ethyl]piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.41 ml of triethylamine is added to a solution of 0.5 g of the compound obtained in EXAMPLE 11, step B), in 10 ml of DCM, the mixture is then cooled to 0° C. and 0.14 ml of benzyl chloroformate is added dropwise. The reaction mixture is washed twice with water, dried over MgSO4 and concentrated under vacuum. The residue is chromatographed on silica gel H using DCM and then a DCM/MeOH mixture (94/6; 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 0.39 g of the expected hydrochloride after crystallization from iso ether. M.p.=135° C.

Workup

  1. washThe reaction mixture is washed twice with water
  2. dry with materialdried 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-7d504e6d31bb4728a49a96e042f2ee0f
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05726313

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes