Hydrochloric Acid → 6-[2-[4-(Acetyl-N-methylamino)-4-phenylpiperid-1-yl]ethyl]-4-benzyl-6-(3,4-dichlorophenyl)morpholin-3-one hydrochloride monohydrate

HRID 1066663ノート

反応式

HRID 1066663 の反応式
O.Cl.C(N1CC(C2C=CC([Cl:37])=C(Cl)C=2)(CCN2CCC(O)(C3C=CC=CC=3)CC2)[O:13]CC1=O)C1C=CC=CC=1.[CH2:40]([N:47]1[CH2:52][C:51]([CH2:61][CH2:62]N2CCC(C3C=CC=CC=3)(O)CC2)([C:53]2[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([Cl:60])[CH:54]=2)[O:50][CH2:49][C:48]1=[O:76])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:89]([N:92]([C:94]1([C:100]2[CH:105]=[CH:104][CH:103]=[CH:102][CH:101]=2)[CH2:99][CH2:98][NH:97][CH2:96][CH2:95]1)[CH3:93])(=[O:91])[CH3:90].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.CCOCC.O>[OH2:13].[ClH:37].[C:89]([N:92]([C:94]1([C:100]2[CH:101]=[CH:102][CH:103]=[CH:104][CH:105]=2)[CH2:95][CH2:96][N:97]([CH2:62][CH2:61][C:51]2([C:53]3[CH:58]=[CH:57][C:56]([Cl:59])=[C:55]([Cl:60])[CH:54]=3)[CH2:52][N:47]([CH2:40][C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:48](=[O:76])[CH2:49][O:50]2)[CH2:98][CH2:99]1)[CH3:93])(=[O:91])[CH3:90]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 227417314-(acetyl-N-methylamino)-4-phenylpiperidine p-toluenesulfonateHCID 1317226224-Benzyl-6-(3,4-dichlorophenyl)-6-[2-(4-hydroxy-4-phenylpiperid-1-yl)ethyl]morpholin-3-one hydrochloride hemihydrate

生成物 1

HCID 212005966-[2-[4-(Acetyl-N-methylamino)-4-phenylpiperid-1-yl]ethyl]-4-benzyl-6-(3,4-dichlorophenyl)morpholin-3-one hydrochloride monohydrate収率 101.6%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1.1 g of the compound obtained in step B of EXAMPLE 14, 1.85 g of 4-(acetyl-N-methylamino)-4-phenylpiperidine p-toluenesulfonate and 1.3 g of K2CO3 in 3 ml of DMF is heated at 80-100° C. for 2 hours. After cooling to RT, the reaction mixture is poured into water and extracted with ether, the organic phase is washed with water and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H using a DCM/HeOH mixture (from 100/1; v/v to 100/4; v/v) as the eluent. The product obtained is dissolved in DCM, a saturated solution of hydrochloric acid in ether is added until the pH is 1, and the precipitate formed is wrung to give 0.62 g of the expected product. M.p.=148-150° C.

後処理

  1. temperatureAfter cooling to RT
  2. extractionextracted with ether
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. customThe product obtained
  8. customthe precipitate formed

出典と根拠

ORDレコード
ord-fffb45c7e307474f98f8c475c24c85fe
出典データセット
uspto-grants-2001_06
特許番号
US06242637B1

反応ノート

読み込み中…