Water → HCID 67809283, compound

HRID 1421865Notes

Reaction equation

HRID 1421865 reaction equation
CS[C:3]([S:15][CH3:16])=[C:4]1[CH2:13][CH2:12][CH:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH2:10]2)[C:5]1=[O:14].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].O>C(#N)C>[CH3:16][S:15][C:3]([N:27]1[CH2:26][CH2:25][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:29][CH2:28]1)=[C:4]1[CH2:13][CH2:12][CH:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH2:10]2)[C:5]1=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 143452tert-Butyl piperazine-1-carboxylateHCID 70254017HCID 70254017, compound

Product 1

HCID 67809283HCID 67809283, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(Bis-methylthiomethylene)-4,5-dihydro-2H-naphthalen 1-one (11.56 g, 46 mmol) and 1-tert-butyloxycarbonylpiperazine (10.3 g, 55 mmol) were refluxed in acetonitrile (300 ml) for 24 h. The mixture was cooled, water (500 ml) added, and extracted with ethyl acetate (3×200 ml). The combined organics were washed with water and brine, dried (MgSO4), evaporated in vacuo, and the resulting oil purified by flash chromatography, eluting with dichloromethane then dichloromethane:methanol (97:3 v/v) to give 2-(methylthio[4-(tert-butyloxycarbonyl)-1-piperazinyl]methylene)-4,5-dihydro-2H-naphthalen-1-one (8.75 g, 49%) as a foam; δ (360 MHz, CDCl3) 1.49 (9H, s, tBu), 3.31 (3H, s, MeS), 2.86-2.94 (4H, m, CCH2CH2C), 3.3-3.5 (8H, m, NCH2CH2N), 7.18 (1H, d, J=7.5 Hz, H-5), 7.30 (1H, t, J=7.5 Hz, H-7), 7.37 (1H, dt, J=1.4 and 7.5 Hz, H-6), 8.10 (1H, dd, J=1.4 and 7.5 Hz, H-8).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (3×200 ml)
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customthe resulting oil purified by flash chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-574716fadde74bff811e6c1fef7c966c
Source dataset
uspto-grants-2000_06
Patent number
US06080745

Reaction notes

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