Carbon Disulfide → HCID 86585990, compound

HRID 1794066Notes

Reaction equation

HRID 1794066 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]O)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=S)=[S:20].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35](Cl)=[O:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CC(C)=O.O>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:35]([S:20][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:12][CH:13]=2)=[O:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 70043(4-(Benzyloxy)phenyl)methanolHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylate

Product 1

HCID 86585990HCID 86585990, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Under argon 84 mg (1.5 mmol) of solid KOH was dissolved at rt in 214 mg (1 mmol) 4-(benzyloxy)-benzyl alcohol and 0.5 ml acetone. Then 76 mg (1.1 mmol) carbon disulfide was added and the mixture thoroughly stirred for 2 h. 323 mg (1.3 mmol) 4-chlorocarbonyl-piperazine-1-carboxylic acid tert-butyl ester was added and the mixture heated at reflux for 8 h. The reaction mixture was cooled to rt, 3 ml of water added and extracted with TBME. The organic phase was washed with water and brine to pH 7, dried over Na2SO4 and evaporated. Purification of the crude product by preparative HPLC on a PRO C18 column with a H2O/MeCN gradient provided 87 mg 4-(4-benzyloxy-benzylsulfanylcarbonyl)-piperazine-1-carboxylic acid tert-butyl ester as colourless powder. 1H-NMR (CDCl3): 1.46 s, 9H; 3.40–3.65 m, 8H; 4.13 s, 2H; 5.04 s, 2H; 6.90 d, 2H and 7.25–7.48 m, 7H.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 8 h
  3. extractionextracted with TBME
  4. washThe organic phase was washed with water and brine to pH 7
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customPurification of the crude product by preparative HPLC on a PRO C18 column with a H2O/MeCN gradient

Sources & evidence

ORD record
ord-0d322334e57f488aa25f5dba837c09c4
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…