Water → Citalopram

HRID 353605

반응식

HRID 353605 반응식
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][Mg]Cl.Cl[CH2:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:14]#[N:15].O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][CH2:5][C:19]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:18]2[C:11](=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)[CH2:10][O:27]1

참가 물질

7

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrileHCID 178483494HCID 178483494, 화합물

생성물 1

HCID 2771Citalopram수율 95%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-dimethylaminopropylmagnesium chloride (1.2M in THF, 84 ml) was added to a cooled solution of 3-chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile (25.0 g) in a mixture of toluene (175 ml) and THF (50 ml) so that the temperature did not raise above −5° C. The mixture was stirred for 2 hours at 0° C. before water (100 ml) and saturated NH4Cl solution were added to adjust the pH to 9. The phases were separated and the aqueous phase was extracted twice with toluene (200 ml). The combined organic phases were washed with water (200 ml) and concentrated in vacuo to give a viscous oil (28.0 g, 95%). Spectral and analytical data were in accordance with the literature.

후처리

  1. temperaturedid not raise above −5° C
  2. additionwere added
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted twice with toluene (200 ml)
  5. washThe combined organic phases were washed with water (200 ml)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8fe10d7afa064bd0b37a5530ba77ebcb
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753433B2

연결된 노트

불러오는 중…