Formic Acid → 4-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-formyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

HRID 3045

반응식

HRID 3045 반응식
[CH:1]([OH:3])=O.Cl.CN(C)CCCN=C=NCC.[C:16]([NH:19][C:20]1([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:25][CH2:24][N:23]([CH:26]([CH2:39][C:40]2[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([C:50]([F:53])([F:52])[F:51])[CH:41]=2)[CH2:27][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH2:29][NH2:30])[CH2:22][CH2:21]1)(=[O:18])[CH3:17].CN1CCOCC1>ClCCl.Cl.O>[C:16]([NH:19][C:20]1([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:21][CH2:22][N:23]([CH:26]([CH2:39][C:40]2[CH:41]=[C:42]([C:50]([F:51])([F:53])[F:52])[CH:43]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:45]=2)[CH2:27][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=2)[CH2:29][NH:30][CH:1]=[O:3])[CH2:24][CH2:25]1)(=[O:18])[CH3:17]

참가 물질

8

반응물 4

HCID 284Formic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 570149314-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

생성물 1

HCID 867523394-(4-Acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-formyl-N-[3,5-bis(trifluoromethyl)benzyl]butylamine

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

To a 0° C. solution of formic acid (0.09 mL) in dichloromethane (3 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23 g) and the mixture stirred for 15 minutes. To this mixture was added a solution of 4-(4-acetamido-4-phenylpiperidino)-2-(3,4-dichlorophenyl)-N-[3,5-bis(trifluoromethyl)benzyl]butyl amine (0.40) and N-methylmorpholine (0.13 mL) in dichloromethane (5 mL). The mixture was allowed to warm to room temperature overnight, and was diluted with 1N hydrochloric acid (5 mL), dichloromethane, and water (5 mL). The layers were separated and the the aqueous phase was extracted with dichloromethane (10 mL). The combined organic layers were washed (brine), dried, and evaporated to afford material which was purified by chromatography with dichloromethane:methanol (20:1) as eluent, to give a hydrate of the title compound (0.206 g); mp 108°-110° C.; NMR: 8.1-7.5 (m,6), 7.3 (m,6), 4.75-4.40 (m,2), 3.75-3.3 (m,4), 3.3-3.0 (m,4), 2.85 (m,1), 1.95 (s,3), 2.25-1.80 (m,4); MS: m/z=688(M+1,100%); TLC: Rf =0.46 (10:1 dichloromethane:methanol). Analysis for C33H33Cl2F6N3O2.1.50 H2O: Calculated: C, 55.39; H, 5.07; N, 5.87; Found: C, 55.38; H, 4.77; N, 5.84.

후처리

  1. customThe layers were separated
  2. extractionthe the aqueous phase was extracted with dichloromethane (10 mL)
  3. washThe combined organic layers were washed (brine)
  4. customdried
  5. customevaporated
  6. customto afford material which
  7. customwas purified by chromatography with dichloromethane:methanol (20:1) as eluent

출처 및 근거

ORD 기록
ord-0f557f1000674f4b902d975b3b805985
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731309

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