N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-1-methylisoquinoline hydrochloride → Veradoline monohydrochloride

HRID 35226노트

반응식

HRID 35226 반응식
[ClH:1].[N+:2]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[C:14]([O:23][CH3:24])[C:15]([O:21][CH3:22])=[CH:16][CH:17]=3)[CH:12]2[CH3:25])=[CH:7][CH:6]=1)([O-])=O>CO.O.[Pd].C(O)C>[ClH:1].[NH2:2][C:5]1[CH:27]=[CH:26][C:8]([CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:17](=[CH:16][C:15]([O:21][CH3:22])=[C:14]([O:23][CH3:24])[CH:13]=3)[CH:12]2[CH3:25])=[CH:7][CH:6]=1

참가 물질

6

반응물 1

HCID 21295821N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-1-methylisoquinoline hydrochloride

생성물 1

HCID 21295811Veradoline monohydrochloride수율 82%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-7,8-dimethoxy-1-methylisoquinoline hydrochloride (66.3 g, 0.17 m) in methanol (1 liter) and water (10 ml) was placed in an 1100 ml pressure bottle and 5% Pd/C catalyst (5.0 g) added under nitrogen. The mixture was hydrogenated at 40 psi in a Parr apparatus for 20 hr. The catalyst was removed by filtration and the solvent evaporated leaving an oily residue. The residue was dissolved in 95% ethanol (300 ml) and after 24 hr a solid had crystallized out which was collected by filtration and air dried giving 44.3 g (82%) of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline monohydrochloride. The free base could be obtained by basifying a solution of this salt with NaOH and extracting with CHCl3. Evaporation of the solvent and crystallization of the resulting oil from cyclohexane gives the base in 80% efficiency as a white solid. Melting point after drying at 60° for 26 hr under high vacuum 102°-103°.

후처리

  1. additionadded under nitrogen
  2. customThe catalyst was removed by filtration
  3. customthe solvent evaporated
  4. customleaving an oily residue
  5. customhad crystallized out which
  6. filtrationwas collected by filtration and air
  7. customdried

출처 및 근거

ORD 기록
ord-e4821c01d1be418d9c84155703fed6c7
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766131

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