Propionyl chloride → N-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-propionamide

HRID 2428130Notes

Reaction equation

HRID 2428130 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].CCN(C(C)C)C(C)C.[C:15]([SiH2:19][O:20][C:21]([CH3:32])([CH3:31])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:25][NH2:26])([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl>[C:15]([SiH2:19][O:20][C:21]([CH3:32])([CH3:31])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:25][NH:26][C:1](=[O:4])[CH2:2][CH3:3])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 1373299203-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine

Product 1

HCID 137328720N-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-propionamideYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Propionyl chloride (2.02 mL, 23.1 mmol) and DIPEA (14.4 mL, 84.0 mL) were added to a sol. of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine (6.00 g, 20.9 mmol) in CH2Cl2 (195 mL). The mixture was stirred for 15 min at rt, and more CH2Cl2 was added. The mixture was washed with aq. sat. NH4Cl (2×), with aq. 1M NaOH (1×) and with brine (1×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:9→3:2) yielded the title compound (5.08 g, 71%). LC-MS: tR=1.09 min; ES+: 383.41.

Workup

  1. washThe mixture was washed with aq. sat. NH4Cl (2×), with aq. 1M NaOH (1×) and with brine (1×)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 1:9→3:2)

Sources & evidence

ORD record
ord-3b59ab8ad8b44d72a3d35ea3bf06496a
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…