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

HRID 1197838Notes

Reaction equation

HRID 1197838 reaction equation
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:14]1([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][NH2:29])[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C.[Cl:47]CCl>>[ClH:47].[ClH:47].[C:14]1([CH2:20][N:21]2[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][NH:29][C:11]([C:1]34[CH2:8][CH:7]5[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]5)[CH2:2]3)[CH2:10]4)=[O:13])[CH2:25][CH2:26]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 5

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 132351-Adamantanecarboxylic acidHCID 76257Diethyl cyanophosphonateHCID 27353312-(4-Benzylpiperazin-1-yl)ethan-1-amine

Product 1

HCID 45262462N-(2-[4-(Phenylmethyl)-1-piperazinyl]ethyl)tricyclo[3,3,1,13,7]-decane-1-carboxamide DihydrochlorideYield 10%

Procedure

To a solution of adamantane-1-carboxylic acid (11.85 g, 0.065 mol) and 2-[4-(phenylmethyl)-1-piperazinyl]ethylamine (12.0 g, 0.054 mol) in dichloromethane (200 mL) at 4° C. was added, with stirring, a solution of diethylcyanophosphonate (11.8 mL, 0.065 mol) in dichloromethane (50 mL), followed by a solution of triethylamine (9.2 mL, 0.065 mol) in dichloromethane (50 mL). The resulting mixture was stirred overnight, during which time it came up to room temperature. The reaction mixture was then washed with 10% aqueous potassium carbonate (200 mL), dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The desired product (TLC on silica gel using 10% methanol/ethyl acetate, Rf=0.33) was isolated by crystallization from hexane and recrystallized from hexane. It was then converted to its dihydrochloride salt with isopropanolic HCl (12.71 g, 52%), mp=259°-260° C.

Workup

  1. stirringThe resulting mixture was stirred overnight, during which time it
  2. customcame up to room temperature
  3. washThe reaction mixture was then washed with 10% aqueous potassium carbonate (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-d8ad2b16c6fa47ad9b6fff6a941deebb
Source dataset
uspto-grants-1994_01
Patent number
US05278160

Reaction notes

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