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Triethylamine → N-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]tricyclo[3,3,1,13,7]decane-1-carboxamide Dihydrochloride Sesquihydrate

HRID 1197834
Notes
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Reaction equation

HRID 1197834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:18]12([C:28]([Cl:30])=[O:29])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.C(N(CC)CC)C>C(Cl)Cl>[OH2:29].[ClH:1].[ClH:30].[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:28]([C:18]34[CH2:27][CH:22]5[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]5)[CH2:25]3)[CH2:19]4)=[O:29])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.[OH2:29].[OH2:29].[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:28]([C:18]34[CH2:27][CH:22]5[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]5)[CH2:25]3)[CH2:19]4)=[O:29])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1.[ClH:1].[ClH:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 35067593-[4-(3-Chlorophenyl)piperazin-1-yl]propan-1-amine

Product 1

HCID 131717306N-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]tricyclo[3,3,1,13,7]decane-1-carboxamide Dihydrochloride Sesquihydrate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of [4-(3-chlorophenyl)piperazinyl]propylamine (1.28 g, 0.005 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (1 g, 0.005 mol) and triethylamine (1 g, 0.01 mol) were added. Stirring was continued at room temperature overnight. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The remaining residue was subjected to preparative HPLC using silica gel column and ethyl acetate as the eluent. The title compound was separated and converted to the dihydrochloride salt with ethanolic HCl (1.5 g), m.p. 209°-210° C.

Workup

  1. washThe methylene chloride solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe title compound was separated

Sources & evidence

ORD record
ord-e08f77cb09c84f7ba360787b619964ff
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05278160

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes