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

HRID 1656364Notes

Reaction equation

HRID 1656364 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH2:15])[CH2:9][CH2:8]1.[C:16]12([C:26]([Cl:28])=[O:27])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.C(N(CC)CC)C>C(Cl)Cl>[OH2:27].[ClH:28].[ClH:28].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C:26]([C:16]23[CH2:25][CH:20]4[CH2:19][CH:18]([CH2:24][CH:22]([CH2:21]4)[CH2:23]2)[CH2:17]3)=[O:27])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 138853581-Piperazineethanamine, 4-(2-pyrimidinyl)-

Product 1

HCID 131717305N-[2-[4-(2-Pyrimidinyl)-1-piperazinyl]ethyl]tricyclo[3,3,1,13,7]decane-1-carboxamide Dihydrochloride Hydrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(2-pyrimidinyl)piperazino]ethylamine (2.0 g, 0.01 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (3.6 g, 0.018 mol) and triethylamine (2.9 g, 0.015 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 hydrate salt with ethanolic HCl (2.4 g), m.p. 237°-239° 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-f5d386fa2611463dadef5277e39c8013
Source dataset
uspto-grants-1993_10
Patent number
US05254552

Reaction notes

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