Water → Citalopram

HRID 353605

反応式

HRID 353605 の反応式
[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

参加物

7

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrileHCID 178483494HCID 178483494、化合物

生成物 1

HCID 2771Citalopram収率 95%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8fe10d7afa064bd0b37a5530ba77ebcb
出典データセット
uspto-grants-2004_06
特許番号
US06753433B2

関連ノート

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