Diisopropylethylamine → HCID 71632163, compound

HRID 337233Notes

Reaction equation

HRID 337233 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[Br:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl>[C:10]([O:14][C:15](=[O:23])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:32]([C:29]2[CH:28]=[CH:27][C:26]([CH2:25][Br:24])=[CH:31][CH:30]=2)(=[O:33])=[O:34])[CH2:19][CH2:18]1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 71632163HCID 71632163, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.99 ml, 5.6 mmol) was added in one portion to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (0.37 g, 1.85 mmol) in DCM (20 ml) at room temperature. To this mixture was added 4-bromomethyl-benzenesulfonyl chloride (0.5 g, 1.85 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time the mixture was diluted with DCM (50 ml) and washed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting solid was collected by filtration, washed with diethyl ether and dried under vacuum to give the title compound (0.56 g, 70% yield) as an off-white solid. Tr=2.12 min, m/z (ES+) (M+Na)+ 457.

Workup

  1. washwashed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with diethyl ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-7c0a003d78464e2db36809a2d9d88e3c
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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