Phenylacetyl chloride → HCID 71060168, compound

HRID 337235Notes

Reaction equation

HRID 337235 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15](=[O:34])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[CH2:35]([C:42](Cl)=[O:43])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[C:10]([O:14][C:15](=[O:34])[NH:16][CH:17]1[CH2:22][CH2:21][N:20]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][NH:33][C:42](=[O:43])[CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH2:19][CH2:18]1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 81531DiisopropylethylamineHCID 71060257HCID 71060257, compound

Product 1

HCID 71060168HCID 71060168, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.17 ml, 1.02 mmol) was added in one portion to a stirred solution of [1-(4-aminomethyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.25 g, 0.68 mmol) in DCM (10 ml) at room temperature. To this mixture was added benzyl carbonyl chloride (0.1 g, 0.68 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 to give the title compound (0.32 g, 97% yield) as a white solid. δH (500 MHz, DMSO) 8.67 (t, J=5.99 Hz, 1 H) 7.66 (d, J=8.20 Hz, 2 H) 7.47 (d, J=8.35 Hz, 2 H) 7.19-7.36 (m, 5 H) 6.85 (d, J=7.25 Hz, 1 H) 4.38 (d, J=5.99 Hz, 2 H) 3.51 (s, 2 H) 3.46 (d, J=11.82 Hz, 2 H) 3.21 (br. s., 1 H) 2.33-2.43 (m, 3 H) 1.76 (d, J=10.56 Hz, 2 H) 1.30-1.45 (m, 12 H).

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

Sources & evidence

ORD record
ord-27c915dfbade46259667426d4912848f
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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