Triethylamine → 1,1-Dimethylethyl 4-(4-morpholinylcarbonyl)-1-piperazinecarboxylate

HRID 1385887Notes

Reaction equation

HRID 1385887 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.[N:14]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CCN(CC)CC>C(Cl)Cl>[N:14]1([C:20]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 100176291,1-Dimethylethyl 4-(4-morpholinylcarbonyl)-1-piperazinecarboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 1-piperazinecarboxylate (2.50 g, 13.42 mmol) in CH2Cl2 (75 mL) cooled in an ice-water bath was added 4-morpholinecarbonyl chloride (1.57 mL, 13.42 mmol) followed by Et3N (3.74 mL, 26.84 mmol), and the reaction mixture was allowed to warm to room temperature. After 15 h, the reaction mixture was washed with 1.0 N HCl (50 mL), saturated NaHCO3 (75 mL), and brie (50 mL), dried, and concentrated to give the title compound (3.80 g, 95%) as a white solid. Mp: 171-173° C. 1H NMR: δ3.69 (t, J=4.9 Hz, 4H, CH2OCH2), 3.46-3.40 (m, 4H, CH2NCH2), 3.28 (t, J=4.9 Hz, 4H, CH2NCH2), 3.25-3.20 (m, 4H, CH2CH2), 1.47 (s, 9H, t-Bu). MS (DCI/CH4): m/z (rel itensity) 300 (MH+, 73), 272 (28), 244 (100), 200 (73). Anal. (C14H25N3O4): C, H, N.

Workup

  1. washthe reaction mixture was washed with 1.0 N HCl (50 mL), saturated NaHCO3 (75 mL), and brie (50 mL)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7adbc448a9d54903aa0c37dfd294413e
Source dataset
uspto-grants-2001_07
Patent number
US06265381B1

Reaction notes

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