Water → 3-(Tritylamino)-2-azepanone

HRID 1269748

Reaction equation

HRID 1269748 reaction equation
C(N(CC)CC)C.[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:28][CH:29]1[CH2:35][CH2:34][CH2:33][CH2:32][NH:31][C:30]1=[O:36].O>C(Cl)(Cl)Cl>[C:14]([NH:28][CH:29]1[CH2:35][CH2:34][CH2:33][CH2:32][NH:31][C:30]1=[O:36])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 1024632H-Azepin-2-one, 3-aminohexahydro-

Product 1

HCID 147292183-(Tritylamino)-2-azepanoneYield 69.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (1.75 ml, 12.6 mmol) and triphenylmethyl chloride (3.50 g, 12.6 mmol) were added to a solution of 3-amino-2-azepanone (1.46 g, 11.4 mmol) in chloroform (44 ml) at room temperature and stirred overnight at room temperature. The reaction mixture was poured into water and then extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain 3-(tritylamino)-2-azepanone (2.93 g, 69%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-5248271c0b0346c89a291907fc79473c
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Linked notes

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