Chloroacetyl chloride → HCID 178445714, compound

HRID 2404111Notes

Reaction equation

HRID 2404111 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH2:16][CH2:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:28][CH2:29][C:30](Cl)=[O:31]>ClCCl>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([C:30](=[O:31])[CH2:29][Cl:28])[CH2:16][CH2:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66926737HCID 66926737, compound

Product 1

HCID 178445714HCID 178445714, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-(4-tert-butyl-cyclohexyloxy)-2,3-dihydro-1H-indole (0.55 g, 2 mmol), triethylamine (0.56 mL, 4 mmol) in dichloromethane (8 mL) was added chloroacetyl chloride (0.2 mL, 2.6 mmol) at 0° C. The solution was stirred from 0° C. to room temperature for 4 hrs. The solution was diluted with dichloromethane and washed with 5% aqueous citric acid, aqueous sodium biocarbonate, and water, dried over MgSO4, and concentrated. The residue was purified with silica gel column eluted with ethyl acetate in hexane to give product (0.37 g, yield: 52%). ESI-MS: 350.2 (M+H)+.

Workup

  1. washwashed with 5% aqueous citric acid, aqueous sodium biocarbonate, and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified with silica gel column
  5. washeluted with ethyl acetate in hexane

Sources & evidence

ORD record
ord-3f245a8da985434899890add946b290d
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

Loading…