Triethylamine → HCID 45265256, compound

HRID 1768966Notes

Reaction equation

HRID 1768966 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][NH2:17])[CH2:11][CH2:10]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>[ClH:30].[ClH:30].[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][NH:17][C:28]([C:18]23[CH2:27][CH:22]4[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]4)[CH2:25]2)[CH2:19]3)=[O:29])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 103991861-(2-Aminoethyl)-4-(2-methoxyphenyl)piperazine

Product 1

HCID 45265256HCID 45265256, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(2-methoxyphenyl)piperazino]ethylamine (2.53 g, 0.01 mol) in 50 mL of methylene chloride, adamantane-1-carboxylic acid chloride (3 g, 0.02 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 =0.65 in 30% methanol/ethyl acetate system) was separated and convened to the dihydrochloride three-quarters hydrate salt with ethanolic HCl (1.6 g), m.p. 206°-212° 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 =0.65 in 30% methanol/ethyl acetate system) was separated

Sources & evidence

ORD record
ord-a783193384d04bb89e9c81a8eac0012b
Source dataset
uspto-grants-1995_01
Patent number
US05380725

Reaction notes

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