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

HRID 1197837Notes

Reaction equation

HRID 1197837 reaction equation
[C:1]12([C:11]([Cl:13])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:14][CH:15]([NH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[N:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:22][CH2:21]1)[CH3:16].C(N(CC)CC)C>ClCCl>[OH2:12].[ClH:13].[ClH:13].[CH3:16][CH:15]([N:17]([CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)[C:11]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:12])[CH3:14].[OH2:12].[OH2:12].[CH3:16][CH:15]([N:17]([CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[N:27]=[CH:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)[C:11]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:12])[CH3:14].[ClH:13].[ClH:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 10682089N-(1-methylethyl)-2-[4-(2-pyrimidinyl)-1-piperazinyl]ethylamine

Product 1

HCID 131717309N-(1-Methylethyl)-N-(2-[4-(2-pyrimidinyl)-1-piperazinyl]ethyl)-tricyclo[3,3,1,13,7]decane-1-carboxamide Dihydrochloride SesquihydrateYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of adamantane-1-carboxylic acid chloride (1.09 g, 0.005 mol) in dichloromethane (25 mL) was added N-(1-methylethyl)-2-[4-(2-pyrimidinyl)-1-piperazinyl]ethylamine (1.27 g, 0.005 mol) in dichloromethane (15 mL) and triethylamine (2.0 mL, 0.014 mol) at room temperature. The resulting solution was stirred at room temperature for 2 days. The reaction mixture was then washed with water (50 mL), dried over anhydrous magnesium sulfate, and concentrated on a rotary evaporator. The desired product (TLC on silica gel using 30% methanol/ethyl acetate as eluant, Rf=0.51) was isolated by chromatography on 200 g of silica gel using 30% methanol/ethyl acetate and converted to the dihydrochloride salt with isopropanolic HCl (1.87 g, 76%); mp=194°-196° C.

Workup

  1. washThe reaction mixture was then washed with water (50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-fe2fdf271aa94ba89d8ce46bad957a04
Source dataset
uspto-grants-1994_01
Patent number
US05278160

Reaction notes

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