4-Nitrobenzenesulfonyl chloride → HCID 56953987, compound

HRID 1841937Notes

Reaction equation

HRID 1841937 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+:27]([C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1)([O-:29])=[O:28]>C1COCC1>[CH2:10]([O:17][C:18](=[O:26])[NH:19][CH:20]1[CH2:25][CH2:24][N:23]([S:36]([C:33]2[CH:32]=[CH:31][C:30]([N+:27]([O-:29])=[O:28])=[CH:35][CH:34]=2)(=[O:37])=[O:38])[CH2:22][CH2:21]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 15143044-Cbz-aminopiperidine

Product 1

HCID 56953987HCID 56953987, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (1.04 ml, 7.0 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid benzyl ester (0.74 g, 3.1 mmol) in THF (10 ml) at room temperature. To this mixture was added 4-nitrophenyl sulfonyl chloride (0.77 g, 3.5 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the solvent was removed under vacuum and the resulting residue was partitioned between ethyl acetate (50 ml) and HCl (50 ml, 1M solution), the organic layer was separated and washed with brine (50 ml) before being dried (MgSO4), filtered and concentrated under vacuum. The resulting white solid was suspended in heptane and collected by filtration, washed with water (50 ml), heptane (50 ml) and TBME (50 ml) before being dried under vacuum to afford the title compound (1.3 g, 100% yield) as a white solid. Tr=2.09 min m/z (ES+) (M+H+) 420.

Workup

  1. customAfter this time the solvent was removed under vacuum
  2. customthe resulting residue was partitioned between ethyl acetate (50 ml) and HCl (50 ml, 1M solution)
  3. customthe organic layer was separated
  4. washwashed with brine (50 ml)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. filtrationcollected by filtration
  9. washwashed with water (50 ml), heptane (50 ml) and TBME (50 ml)
  10. custombefore being dried under vacuum

Sources & evidence

ORD record
ord-4abd7065138a4d6b8e07e3c38b4b2e48
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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