2,5-Dichloronitrobenzene → Escitalopram

HRID 1669961

반응식

HRID 1669961 반응식
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][CH2:5][C@@:6]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH2:23]O)([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[OH:7].CC(C)([O-])C.[K+].ClC1C=CC(Cl)=CC=1[N+]([O-])=O.O.O.[C:45]([OH:50])(=[O:49])[C:46]([OH:48])=[O:47]>O1CCCC1.CC(C)=O.O>[CH3:25][N:2]([CH2:3][CH2:4][CH2:5][C@@:6]1([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[O:7][CH2:23][C:16]2[CH:17]=[C:18]([C:19]#[N:20])[CH:21]=[CH:22][C:15]1=2)[CH3:1].[C:46]([OH:48])([C:45]([OH:50])=[O:49])=[O:47].[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][CH2:5][C@:6]1([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:15]2[C:16](=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=2)[CH2:23][O:7]1

참가 물질

9

반응물 4

HCID 69772,5-DichloronitrobenzeneHCID 61373Oxalic acid dihydrateHCID 7472057Citadiol, (S)-HCID 23665647Potassium tert-butoxide

생성물 2

HCID 146570EscitalopramHCID 146571Escitalopram Oxalate

시약·촉매·용매 3

HCID 180Acetone용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 6 gm of (S)-(−)-4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)benzonitrile in 60 ml tetrahydrofuran (THF) was added 4.33 gm of potassium tertiary butoxide at 0-10° C. and stirred for 30 minutes. A solution of 4.04 gm of 2,5-dichloronitrobenzene in 30 ml THF at 0-10° C. was added to it and stirred for 10-15 hours at room temperature, followed by addition of 250 ml of water. The reaction mixture was extracted with toluene, the toluene layer was washed with water and 5% sodium hydroxide solution and after acid base treatment yielded an oily product. The oil was dissolved in 16 ml of acetone at 30° C. and 1.75 gm of oxalic acid dihydrate in 8 ml acetone was added to it, stirred, cooled, filtered and dried at 60° C. to get the oxalic acid salt of (S)-(+)-1-[3-(dimethylamino) propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile.

후처리

  1. stirringstirred for 10-15 hours at room temperature
  2. extractionThe reaction mixture was extracted with toluene
  3. washthe toluene layer was washed with water and 5% sodium hydroxide solution
  4. customafter acid base treatment yielded an oily product
  5. stirringstirred
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried at 60° C.

출처 및 근거

ORD 기록
ord-6c65327698f545e2aa4c6b9ca64f2185
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989645B2

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