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

HRID 1368164Notes

Reaction equation

HRID 1368164 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bae55b2503e64d7d97f2af4752714de4
Source dataset
uspto-grants-2003_06
Patent number
US06573262B2

Reaction notes

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