tert-Butanol → HCID 86595132, compound

HRID 969552Notes

Reaction equation

HRID 969552 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].Cl[S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8].[Cl:13][C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][C:32]=1[Cl:33])[O:17][CH:18]1[CH2:23][CH2:22][N:21]([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:20][CH2:19]1.C(N(CC)CC)C>ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([CH:30]=[CH:31][C:32]=1[Cl:33])[O:17][CH:18]1[CH2:19][CH2:20][N:21]([CH:24]2[CH2:25][CH2:26][N:27]([S:7]([NH:10][C:11](=[O:12])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:9])=[O:8])[CH2:28][CH2:29]2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

Product 1

HCID 86595132HCID 86595132, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

tert-Butanol (0.48 ml) in dichloromethane (2 ml) was added to a solution of chlorosulfonylisocyanate (0.43 ml) in dichloromethane (5 ml) stirring at 0° C. The resulting solution was then added to a solution of 4-(3,4-dichlorophenoxy)-1,4′-bipiperidine (1.6 g) and triethylamine (0.77 ml) in dichloromethane (20 ml) at 0° C. After stirring at 0° C. for 2 h, the reaction mixture was washed with 0.1M hydrochloric acid (30 ml), dried (MgSO4) and evaporated. The residue was triturated with diethylether (20 ml) to give the title compound as a white solid. (1.9 g)

Workup

  1. stirringAfter stirring at 0° C. for 2 h
  2. washthe reaction mixture was washed with 0.1M hydrochloric acid (30 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated with diethylether (20 ml)

Sources & evidence

ORD record
ord-0e9ebc0b8b87447681b9bb90eaebebea
Source dataset
uspto-grants-2007_12
Patent number
US07307090B2

Reaction notes

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