Triethylamine → [4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(2-methanesulfonyl-phenyl)-methanone

HRID 349743노트

반응식

HRID 349743 반응식
C(Cl)(=O)C(Cl)=O.[CH3:7][S:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=O)(=[O:10])=[O:9].[Cl:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[Cl:40])[O:24][CH:25]1[CH2:30][CH2:29][N:28]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:27][CH2:26]1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[Cl:40])[O:24][CH:25]1[CH2:26][CH2:27][N:28]([CH:31]2[CH2:32][CH2:33][N:34]([C:13]([C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:8]([CH3:7])(=[O:9])=[O:10])=[O:15])[CH2:35][CH2:36]2)[CH2:29][CH2:30]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2843422-Methanesulfonylbenzoic acidHCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

생성물 1

HCID 22397458[4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidinyl-1'-yl]-(2-methanesulfonyl-phenyl)-methanone수율 76.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매4회

실험 절차

Oxalyl chloride (55 ml, 0.63 mol) was added dropwise over 10 minutes to a stirred suspension of 2-methanesulfonyl-benzoic acid (7.1 g, 0.036) in DCM (550 ml) containing DMF (0.5 ml). The solution was then stirred for 2 hours at room temperature. The solution was then evaporated to give a solid that was redissolved in dichloromethane and again evaporated to give a yellow solid. The solid acid chloride was dissolved in DCM (275 ml) and was added over 10 minutes to a stirred solution of the product of Step 3 (11.0 g, 0.033 mol) and triethylamine (15.4 ml, 0.11 mol) in dichloromethane (125 ml). The resultant solution was stirred at room temperature for 16 hours. The solution was then washed with water (500 ml), 1M aq NaOH (500 ml) and water (2×500 ml). The organic phase was dried (MgSO4), filterered and the solvent removed to give a pale yellow foam. The foam was triturated with diethyl ether to give the title compound (12.96 g, 76%).

후처리

  1. customThe solution was then evaporated
  2. customto give a solid
  3. customagain evaporated
  4. customto give a yellow solid
  5. washThe solution was then washed with water (500 ml), 1M aq NaOH (500 ml) and water (2×500 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent removed
  8. customto give a pale yellow foam
  9. customThe foam was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-3c0d8bcb0d2e4b9db065c0414a32c98b
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179922B2

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