HCID 54538528, compound → HCID 53864393, compound

HRID 1976156Notes

Reaction equation

HRID 1976156 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=2[Cl:29])[CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[Cl:29][C:23]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=1[CH2:21][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[CH:11]1[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 54538528HCID 54538528, compound

Product 1

HCID 53864393HCID 53864393, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(tert-butyloxycarbonyl)-4-{[(2,5-dichlorophenyl)methyl]piperid-1-yl}hexahydro4 H-azepine (700 mg, 1.58 mmol) in trifluoroacetic acid (2 ml) and methylene chloride (0.5 ml) was stirred at room temperature for 15 min. The solution was concentrated in vacuo and the residue was dissolved in chloroform and extracted with saturated aqueous sodium carbonate. The chloroform extract was dried over sodium sulfate and concentrated in vacuo to give 4-{[(2,5-dichlorophenyl)methyl]piperid-1-yl}hexahydro-4 H-azepine (489 mg, 90%).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. extractionextracted with saturated aqueous sodium carbonate
  4. extractionThe chloroform extract
  5. dry with materialwas dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-923789d61e644607b8377cfd1f82406b
Source dataset
uspto-grants-2001_05
Patent number
US06225324B1

Reaction notes

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