1,2-Dichloroethane → Tert-butyl 4-(4-chloro-3-cyanobenzoyl)piperazine-1-carboxylate

HRID 1169592노트

반응식

HRID 1169592 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]#[N:12].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:23]2[CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24]2)=[O:8])=[CH:4][C:3]=1[C:11]#[N:12]

참가 물질

7

반응물 5

HCID 111,2-Dichloroethane2회HCID 8471Triethylamine2회HCID 757711-Hydroxybenzotriazole2회HCID 143452tert-Butyl piperazine-1-carboxylateHCID 226446124-Chloro-3-cyanobenzoic acid

생성물 1

HCID 68766029Tert-butyl 4-(4-chloro-3-cyanobenzoyl)piperazine-1-carboxylate수율 96.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a 100 mL round-bottom flask under a positive nitrogen pressure of 4-chloro-3-cyanobenzoic acid (4.28 mmol), 1-(tert-butoxycarbonyl)piperazine (1.59 g, 8.56.mmol), EDC (903 mg, 4.71 mmol) and HOBT (694 mg, 5.14 mmol) were dissolved in 17 mL of CH2Cl2. Triethylamine (1.5 mL, 10.7 mmol) was added and the reaction mixture was stirred for 20 h. After this time additional quantities of EDC (411 mg, 2.14 mmol), HOBT (290 mg, 2.14 mmol) and triethylamine (300 □L, 2.14 mmol) were added. After stirring for an additional 20 h the reaction mixture was washed with 6 mL portions of: 10% KHSO4, water, saturated NaHCO3, and saturated NaCl. The organic extracts were dried over Na2SO4, filtered and concentrated to afford 1.44 g of tert-butyl 4-(4-chloro-3-cyanobenzoyl)piperazine-1-carboxylate as a beige solid.

후처리

  1. stirringAfter stirring for an additional 20 h the reaction mixture
  2. washwas washed with 6 mL portions of: 10% KHSO4, water, saturated NaHCO3, and saturated NaCl
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c05d769a2c6c453ebedc391aa43fa115
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825120B2

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