HCID 21077868, compound → Methyl 3-(2-phenoxyethyl)-1-piperazinecarboxylate

HRID 1374742Notes

Reaction equation

HRID 1374742 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH:9]1[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH3:17][O:16][C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([CH2:18][CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10]1)=[O:15]

Participants

4

Reactant 1

HCID 21077868HCID 21077868, compound

Product 1

HCID 21077876Methyl 3-(2-phenoxyethyl)-1-piperazinecarboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (RS)-1-(tert-butyloxycarbonyl)-4-methoxycarbonyl-2-(2-phenoxyethyl)piperazine (D8) (1.4 g, 3.85 mmol) in dichloromethane (30 ml) and trifluoroacetic acid (5 ml) was stirred at 35° C. for 0.75 h. On cooling, the mixture was evaporated in vacuo and the residue partitioned between dichloromethane and 1N sodium hydroxide (50 ml each). The organic layer was dried (Na2SO4) and evaporated in vacuo to afford the title compound as a colourless oil (1.01 g, 99%). Mass spectrum (AP+): Found 265 (MH+). C14H20N2O3 requires 264.

Workup

  1. temperatureOn cooling
  2. customthe mixture was evaporated in vacuo
  3. customthe residue partitioned between dichloromethane and 1N sodium hydroxide (50 ml each)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-097ee3cb682b4f32980c7d5684c44756
Source dataset
uspto-grants-2007_01
Patent number
US07166608B2

Reaction notes

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