Diisopropylethylamine → HCID 23589141, compound

HRID 489907Notes

Reaction equation

HRID 489907 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([N:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)=[O:28])[CH2:22]4)[CH2:17][CH2:16]3)=[O:14])[CH:10]=[C:9]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[N:50]1([C:56](Cl)=[O:57])[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1>ClCCl>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]([N:15]3[CH2:16][CH2:17][CH:18]([N:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([C:27]([N:29]5[CH2:34][CH2:33][N:32]([C:56]([N:50]6[CH2:55][CH2:54][O:53][CH2:52][CH2:51]6)=[O:57])[CH2:31][CH2:30]5)=[O:28])[CH2:22]4)[CH2:19][CH2:20]3)=[O:14])[CH:10]=[C:9]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chloride2×HCID 23589145HCID 23589145, compound

Product 1

HCID 23589141HCID 23589141, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R)-(2,6-Diphenyl-pyridin-4-yl)-[3-(piperazine-1-carbonyl)-[1,4′]bipiperidinyl-1′-yl]-methanone (0.507 mmol, 272 mg) was dissolved in anhydrous dichloromethane and N,N-diisopropylethylamine (2 eq. 180 μl) followed by N-morpholine carbonyl chloride (1 eq. 60 μl ) were added. After 3 hr a further aliquot of N-morpholine carbonyl chloride (40 μl) was added and the mixture was stirred at room temperature for 66 hr. The solution was washed with 0.1M sodium hydroxide solution, dried over anhydrous sodium sulfate, diluted with toluene and evaporated to dryness. The product was purified by chromatography on silica gel eluting with a 2.5% to 10% methanol-dichloromethane gradient to give the title compound (270 mg, 82%).

Workup

  1. additionwere added
  2. washThe solution was washed with 0.1M sodium hydroxide solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. additiondiluted with toluene
  5. customevaporated to dryness
  6. customThe product was purified by chromatography on silica gel eluting with a 2.5% to 10% methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-b0c1f6dde7ff4eb0a6d44c45cd0815ba
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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