Triethylamine → HCID 18697974, compound

HRID 2289554Notes

Reaction equation

HRID 2289554 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH2:15][CH:11]([C:12]([OH:14])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[Cl:30][C:31]1[N:36]=[CH:35][N:34]=[C:33]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:32]=1.C(N(CC)CC)C>O1CCCC1.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:12]([N:40]2[CH2:41][CH2:42][N:37]([C:33]3[CH:32]=[C:31]([Cl:30])[N:36]=[CH:35][N:34]=3)[CH2:38][CH2:39]2)=[O:14])[CH2:15][CH2:16]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 186979794-Chloro-6-(piperazin-1-yl)pyrimidine hydrochloride

Product 1

HCID 18697974HCID 18697974, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-tert-butoxycarbonyl isonipecotic acid (12.93 g) in tetrahydrofuran (250 ml) at 0° C. was added a solution of carbonyldiimidazole (8.32 g) in tetrahydrofuran (70 ml). The resulting solution was stirred at ambient temperature for 2 hours. This solution was cooled to 0° C. and a solution of (6-chloro-pyrimidin-4-yl)piperazine hydrochloride (13.25 g) and triethylamine (23.57 ml) in dichloromethane (200 ml) added dropwise over 20 minutes. The suspension obtained was stirred at ambient temperature for 18 hours. The mixture was diluted with dichloromethane and washed with water, 2M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution, dried (Na2SO4) and evaporated to give 1-(tert-butoxycarbonyl)-4-[4-(6-chloro-pyrimidin-4-yl)piperazin-1-ylcarbonyl]piperidine (17.45 G) as a cream solid.

Workup

  1. temperatureThis solution was cooled to 0° C.
  2. customThe suspension obtained
  3. stirringwas stirred at ambient temperature for 18 hours
  4. washwashed with water, 2M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c288009080c942d5a684715adf97d185
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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