Diisopropylethylamine → N-[4-(methylcarbonylamino)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

HRID 378505

반응식

HRID 378505 반응식
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)([OH:17])[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[CH3:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41]Cl)=[CH:37][CH:36]=1)=[O:33].C(N(CC)C(C)C)(C)C>CS(C)=O>[CH3:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][N:14]2[CH2:15][CH2:16][CH:11]([C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:29])([F:1])[F:30])=[CH:9][CH:8]=3)([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:20][CH:19]=3)[OH:17])[CH2:12][CH2:13]2)=[CH:37][CH:36]=1)=[O:33]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 148705Acetamide, N-(4-(chloromethyl)phenyl)-HCID 190409264-[Bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine

생성물 1

HCID 15515182N-[4-(methylcarbonylamino)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine수율 64.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a stirred solution of 0.4 gram (0.0008 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine in 10 mL of dimethyl sulfoxide was added a mixture of 0.2 gram (0.0008 mole) of 4-(methylcarbonylamino)phenylmethyl chloride and 0.6 mL (0.003 mole) of N,N-diisopropylethylamine. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was partitioned between an aqueous solution saturated with sodium bicarbonate and ethyl acetate. The organic layer was separated and washed with an aqueous solution saturated with sodium chloride. The organic layer was then concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with methylene chloride and mixtures of 10-50% acetone in methylene chloride as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about 0.3 gram of N-[4-(methylcarbonylamino)phenylmethyl]-4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionUpon completion of addition
  2. customAfter this time the reaction mixture was partitioned between an aqueous solution saturated with sodium bicarbonate and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with an aqueous solution saturated with sodium chloride
  5. concentrationThe organic layer was then concentrated under reduced pressure to a residue, which
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3a58e6bb948f417397797c328a2af1ba
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030987

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