Triethylamine → HCID 131716829, compound

HRID 1030608Notes

Reaction equation

HRID 1030608 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]1.[C:19]12([C:29]([Cl:31])=[O:30])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.C(N(CC)CC)C>C(Cl)Cl>[OH2:2].[ClH:31].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:29]([C:19]23[CH2:28][CH:23]4[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]4)[CH2:26]2)[CH2:20]3)=[O:30])[CH2:13][CH2:14]1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:29]([C:19]23[CH2:28][CH:23]4[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]4)[CH2:26]2)[CH2:20]3)=[O:30])[CH2:13][CH2:14]1.[ClH:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 104672591-(3-Aminopropyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 131716829HCID 131716829, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(2-methoxyphenyl)piperazinyl]propylamine (2.5 g, 0.01 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (2.02 g, 0.010 mol) and triethylamine (2 g, 0.02 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. In repeated preparations, the residue was dissolved in ethyl acetate (10 mL) and subjected to flash chromatography using a 9 inch column of silica gel and ethyl acetate as the eluent. The title compound (TLC Rf =0.53 in 30% methanol/ethyl acetate system) was separated and converted to the hydrochloride hemihydrate salt with ethanolic HCl (2.3 g), m.p. 186°-190° 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. dissolutionIn repeated preparations, the residue was dissolved in ethyl acetate (10 mL)
  5. customThe title compound (TLC Rf =0.53 in 30% methanol/ethyl acetate system) was separated

Sources & evidence

ORD record
ord-bd4ca3b9e5004282b5f95444b547e90e
Source dataset
uspto-grants-1992_04
Patent number
US05106849

Reaction notes

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