Acetic Acid → HCID 67508190, 화합물

HRID 1468161

반응식

HRID 1468161 반응식
[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

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydride2회HCID 114809021-(3-Cyanophenyl)piperazine

생성물 1

HCID 67508190HCID 67508190, 화합물수율 80.5%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8d4599e273644e549f60421d34e908be
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000154B2

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