1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone → 4-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

HRID 1449056노트

반응식

HRID 1449056 반응식
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][N:17]3[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:24]([Li])([CH3:27])([CH3:26])[CH3:25]>C1C=CC=CC=1>[C:24]([C:20]1([OH:23])[CH2:21][CH2:22][N:17]([CH2:16][CH:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)[CH2:18][CH2:19]1)([CH3:27])([CH3:26])[CH3:25]

참가 물질

4

반응물 2

HCID 125156511-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinoneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 30532464-Piperidinol, 4-(t-butyl)-1-((10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-, (+-)-

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

Solution of 5 parts of 1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)methyl]-4-piperidinone in 150 parts by volume of benzene is added dropwise over a period of 50 minutes to a stirred, cooled solution of tert-butyllithium (33.8 parts by volume of 1.9 M ethyl ether solution) in 150 parts by volume of benzene under a nitrogen atmosphere. The resultant solution is stirred at ambient temperature for about 1 hour and quenched with the addition of 100 parts by volume of 10% ammonium chloride. The solution is stirred for additional 2 hours, the organic layer separated, washed with brine, dried with magnesium sulfate and concentrated in vacuo to give clear yellow oil. This oil is chromatographed on silica gel using 1% ethanol/methylene chloride as eluent to afford 4-tert-butyl-1-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-methyl]-4-piperidinol melting at about 96°-98.5° C. This compound is represented by the following general formula ##STR27##

후처리

  1. customquenched with the addition of 100 parts by volume of 10% ammonium chloride
  2. customthe organic layer separated
  3. washwashed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give clear yellow oil
  7. customThis oil is chromatographed on silica gel using 1% ethanol/methylene chloride as eluent

출처 및 근거

ORD 기록
ord-e2be669a4610486fa344b8190abf42fd
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04188485

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