Acetic Acid → HCID 67508190、化合物

HRID 1468161

反応式

HRID 1468161 の反応式
[N:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[C:10]#[N:11])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].Cl>ClC(Cl)C>[CH3:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:14]=[CH:13][CH:12]=[C:9]([C:10]#[N:11])[CH:8]=3)[CH2:2][CH2:3]2)[CH:19]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydride2 回HCID 114809021-(3-Cyanophenyl)piperazine

生成物 1

HCID 67508190HCID 67508190、化合物収率 80.5%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Dissolve 3-piperazin-1-yl-benzonitrile (0.19 g, 1.00 mmol), 3-formyl-benzoic acid methyl ester (0.33 g, 2.00 mmol) and AcOH (0.64 mL, 10.0 mmol) in 5 mL dichloroethane. Add NaBH(OAc)3 (0.42 g, 2.00 mmol) and stir the mixture overnight. Add another portion of NaBH(OAc)3 (0.42 g, 2.00 mmol) and stir the mixture an additional 24 h. Concentrate the crude reaction mixture under a stream of N2. Dissolve the residue into 5% HCl and apply to a Dowex column. Wash the column with 1×50 mL 5% HCl, 2×50 mL H2O, 2×50 mL of MeOH and 2×50 mL of dichloromethane. Liberate the basic residues by washing the resin with 3×30 mL of 10% NH3/MeOH and 2×20 mL of dichloromethane. Concentrate the basic washings to give 0.27 g of 3-[4-(3-cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid methyl ester as a clear oil. 1H NMR indicates some contamination with starting amine. The mixture is carried on without further purification.

後処理

  1. concentrationConcentrate the crude
  2. customreaction mixture under a stream of N2
  3. washWash the column with 1×50 mL 5% HCl, 2×50 mL H2O, 2×50 mL of MeOH and 2×50 mL of dichloromethane
  4. washby washing the resin with 3×30 mL of 10% NH3/MeOH and 2×20 mL of dichloromethane
  5. concentrationConcentrate the basic washings

出典と根拠

ORDレコード
ord-8d4599e273644e549f60421d34e908be
出典データセット
uspto-grants-2015_04
特許番号
US09000154B2

関連ノート

読み込み中…