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Diisopropylethylamine → N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine

HRID 850377
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HRID 850377 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12]Cl)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[F:14][C:15]([F:41])([F:40])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)([OH:29])[CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.C(Cl)Cl.CC(C)=O.CCCCCCC>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:26]3[CH2:27][CH2:28][CH:23]([C:22]([C:30]4[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:35]=4)([C:19]4[CH:20]=[CH:21][C:16]([C:15]([F:14])([F:40])[F:41])=[CH:17][CH:18]=4)[OH:29])[CH2:24][CH2:25]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 3

HCID 81531DiisopropylethylamineHCID 193637461-(Chloromethyl)-4-(cyclopropylmethoxy)benzeneHCID 19363748HCID 19363748, 화합물

생성물 1

HCID 11837562N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine수율 71%

시약·촉매·용매 4

HCID 180Acetone용매
HCID 679
Dimethyl Sulfoxide
용매
HCID 6344Dichloromethane용매4회
HCID 8900Heptane용매2회

실험 절차

This compound was prepared in a manner analogous to that of Step D of Example 3, with 0.4 gram (0.002 mole) of 4-(cyclopropylmethoxy)phenylmethyl chloride (prepared as in Step A of Example 16), 0.9 gram (0.002 mole) of 4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine, and 1.1 grams (0.008 mole) of N,N-diisopropylethylamine in about 30 mL of dimethyl sulfoxide as reagents The crude reaction product was subjected to column chromatography on silica gel with 1:1 heptane:methylene chloride, pure methylene chloride, 11:10 heptane:methylene chloride, and 1:10 acetone:methylene chloride used succesively as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.8 gram of N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine. The NMR spectrum was consistent with the proposed structure.

후처리

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 3
  2. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4ac9281763b24a389847910cc27726a7
출처 데이터셋
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06017931

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