Benzoyl chloride → HCID 89824982, compound

HRID 2273852Notes

Reaction equation

HRID 2273852 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 71580561HCID 71580561, compound

Product 1

HCID 89824982HCID 89824982, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(6-((tert-butyldimethylsilyl)oxy)hexyl)cyclohexanamine (208 mg, 0.66 mmol) and triethyl amine (0.19 mL, 1.32 mmol) in methylene chloride (5 mL) at 0° C. was added benzoyl chloride (0.092 mL, 0.80 mmol). The mixture was stirred for 2 hours before it was diluted with ethyl acetate and washed with saturated bicarbonate solution nd brine. The organic phase was separated and concentrated. Purification on silica gel with ethyl acetate: hexanes from 0:1 to 2:8 provided desired product as a clear oil (242.2 mg, 88%). 1H NMR (300 MHz, CDCl3): δ 7.40-7.20 (m, 5H), 3.64-2.95 (m, 5H), 1.95-0.88 (m, 18H), 0.83 (s, 9H), 0.00 (s, 6H).

Workup

  1. washwashed with saturated bicarbonate solution nd brine
  2. customThe organic phase was separated
  3. concentrationconcentrated
  4. customPurification on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-c2057b898405412ca2e1694b5c930ee9
Source dataset
uspto-grants-2015_09
Patent number
US09126937B2

Reaction notes

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