Water → Citalopram

HRID 353606노트

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HRID 353606 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][Mg]Cl.O>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH3:30])[CH2:25][CH2:26][CH2:27][C:14]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:13]2[C:12](=[CH:20][C:19]([C:21]#[N:22])=[CH:18][CH:17]=2)[CH2:11][O:15]1

참가 물질

6

반응물 4

HCID 962WaterHCID 113449102-(Chloromethyl)-4-cyanobenzoyl chlorideHCID 178418676HCID 178418676, 화합물HCID 178483494HCID 178483494, 화합물

생성물 1

HCID 2771Citalopram수율 56%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 4-fluoro phenylmagnesium bromide (0.7M in THF, 16 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (1.75 g) in toluene (20 ml) so that the temperature did not rise above 0° C. After 40 minutes a solution of 3-dimethylaminopropylmagnesium chloride (0.85M in THF, 10 ml) was added so that the temperature did not rise above 2° C. The mixture was stirred for 30 minutes, and water (30 ml) was added. The pH of the mixture was adjusted to 4.5, and the phases were separated. The pH of the aqueous phase was adjusted to 8 and extracted with toluene (30 ml) and 2-propanol (10 ml). The organic phase was concentrated in vacuo to give a viscous oil (1.5 g, 56%). Spectral and analytical data were in accordance with the literature.

후처리

  1. customdid not rise above 0° C
  2. customdid not rise above 2° C
  3. customthe phases were separated
  4. extractionextracted with toluene (30 ml) and 2-propanol (10 ml)
  5. concentrationThe organic phase was concentrated in vacuo

출처 및 근거

ORD 기록
ord-fdbe8ba119124664ab19837e8f59784a
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753433B2

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