Triethylamine → N-[2-[4-(3-Chlorophenyl)-1-piperazinyl]ethyl]tricyclo[3,3,1,13,7]decane-1-carboxamide Dihydrochloride

HRID 1656366Notes

Reaction equation

HRID 1656366 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:17]12([C:27]([Cl:29])=[O:28])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2.C(N(CC)CC)C>C(Cl)Cl>[ClH:1].[ClH:29].[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][NH:16][C:27]([C:17]34[CH2:26][CH:21]5[CH2:20][CH:19]([CH2:25][CH:23]([CH2:22]5)[CH2:24]3)[CH2:18]4)=[O:28])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 127267362-(4-(3-Chlorophenyl)piperazin-1-yl)ethan-1-amine

Product 1

HCID 45262376N-[2-[4-(3-Chlorophenyl)-1-piperazinyl]ethyl]tricyclo[3,3,1,13,7]decane-1-carboxamide Dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(m-chlorophenyl)piperazino]ethylamine (2.5 g, 0.01 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (5 g, 0.018 mol) and triethylamine (3.6 g, 0.018 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 dissolved in ethyl acetate (10 mL) and subjected to column chromatography using silica gel and ethyl acetate as the eluent. The title compound was separated and converted to the dihydrochloride salt with ethanolic HCl (0.7 g), m.p. 210°-213° 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. dissolutionThe remaining residue was dissolved in ethyl acetate (10 mL)
  5. customThe title compound was separated

Sources & evidence

ORD record
ord-1a1aa8c489a54a09b16ef03b997a91ce
Source dataset
uspto-grants-1993_10
Patent number
US05254552

Reaction notes

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