Acetic Acid → Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylate

HRID 1990909

반응식

HRID 1990909 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClC(Cl)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 114773-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 4316940Tert-butyl 4-[(3-chlorophenyl)methyl]piperazine-1-carboxylate수율 87.4%

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of piperazine-1-carboxylic acid tert-butyl ester (4.00 g, 21.5 mmol) in dry dichloroethane (70 mL) are added 3-chlorobenzaldehyde (2.49 mL, 3.08 g, 21.9 mmol), HOAc (2.58 mL, 2.71 g, 45.1 mmol) and NaBH(OAc)3 (5.46 g, 25.8 mmol) at ambient temperature. After stirring at ambient temperature for 3d, 2N NaOH (40 mL) is added, the layers are separated, and the aqueous layer is extracted with CH2Cl2 (4×50 mL). The combined organic extracts are washed with water (3×50 mL) and brine (80 mL) and dried over MgSO4. The crude material is purified by chromatography on silica gel, eluting with hexane:EtOAc mixtures, yielding 5.83 g (18.8 mmol, 87%) of the title compound as yellow oil. MS (ES): m/z 311.0/313.0 (50/18) [MH+]. tR (method A)=5.0 min.

후처리

  1. additionis added
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted with CH2Cl2 (4×50 mL)
  4. washThe combined organic extracts are washed with water (3×50 mL) and brine (80 mL)
  5. dry with materialdried over MgSO4
  6. customThe crude material is purified by chromatography on silica gel
  7. washeluting with hexane

출처 및 근거

ORD 기록
ord-994156a864ae422b9ebe21fde113ac5d
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645754B2

연결된 노트

불러오는 중…