1,2-Dichloroethane → 1-Piperazinecarboxylic acid, 4-benzoyl-, 1,1-diMethylethyl ester

HRID 1368164노트

반응식

HRID 1368164 반응식
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:14](O)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:14]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 243Benzoic AcidHCID 143452tert-Butyl piperazine-1-carboxylate

생성물 1

HCID 185197561-Piperazinecarboxylic acid, 4-benzoyl-, 1,1-diMethylethyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Prepared in the same manner as intermediate 18. To a solution of tert-butyl 1-piperazinecarboxylate (15.0 g. 80.5 mmol) and benzoic acid (8.94 g, 73.2 mmol) in CH2Cl2 (500 mL), was added DMAP (9.84 g, 80.5 mmol) and EDC (15.39 g, 80.5 mmol). The reaction mixture was stirred at rt for 17 h, and then washed with excess hydrochloric acid (5×250 mL, 1 N aq.) and water (350 mL). The organic layer was dried (MgSO4) and evaporated in vacuo to give N-Benzoyl-N′-Boc piperazine as an off white solid (21 g, 99%). 1H NMR (300 MHz, CD3OD) δ 7.46 (m, 5H), 3.80-3.30 (b m, 8H), 1.47 (s, 9H); LC/MS (ES+) m/z (M+H)+=291, (2M+H)+=581, HPLC Rt=1.430.

후처리

  1. customPrepared in the same manner as intermediate 18
  2. washwashed with excess hydrochloric acid (5×250 mL, 1 N aq.) and water (350 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-bae55b2503e64d7d97f2af4752714de4
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573262B2

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