Toluene → Sertraline

HRID 1393711

反応式

HRID 1393711 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[N:19][CH3:20])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C1(C)C=CC=CC=1.[H][H]>[Ni].ClC1C=CC=CC=1Cl>[CH3:20][NH:19][C@@H:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10][CH2:11]1

参加物

6

反応物 3

HCID 1140TolueneHCID 9796475N-(4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene)methanamineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 68617Sertraline収率 0.8%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 72391,2-Dichlorobenzene溶媒

実験手順

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)naphthalenylidene]methanamine (Ketimine) (50 g), toluene (300 ml), Raney Nickel (0.15 g wet basis) and o-dichlorobenzene (25 ml) are charged into a reaction vessel. The mixture is hydrogenated at 5 to 6 kg/cm2 over pressure of hydrogen for 6 to 7 hrs at about 28 to 30° C. The catalyst is removed by filtration and the cake is washed with 50 ml methanol. The cis to trans ratio is 75 to 80/25 to 20. The amount of dehalogenated by product is <0.1%. Sertraline racemate free base thus formed is treated with hydrochloric acid (24 ml, 33%) and predominantly isomer of sertraline HCl racemate is filtered [Cis>95%, trans<5%, dehalogenation product<0.1%, yield 0.80 to 0.82%].

後処理

  1. customThe catalyst is removed by filtration
  2. washthe cake is washed with 50 ml methanol

出典と根拠

ORDレコード
ord-e23c1c27ded142448ba0d72101363364
出典データセット
uspto-grants-2008_03
特許番号
US07345201B2

関連ノート

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