Benzhydrylamine → HCID 69028747, compound

HRID 272794Notes

Reaction equation

HRID 272794 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:16]([O:18]C1C=CC([N+]([O-])=O)=CC=1)=[O:17].C([N:31](C(C)C)CC)(C)C.N[CH:38]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(#N)C>[C:16](=[O:17])([O:18][C:38]([CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[NH2:31]

Participants

6

Reactant 4

HCID 7036BenzhydrylamineHCID 784611-Benzylpiperidin-4-olHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 69028747HCID 69028747, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Benzyl-4-piperidinol (2.09 g, 10.9 mmol) and 4-nitrophenyl chloroformate (2.2 g, 10.9 mmol) were dissolved in anhydrous acetonitrile (10 mL). To this solution was added diisopropylethylamine (1.4 g, 10.9 mmol) and the resulting yellow solution was stirred at room temperature. After 3 h, aminodiphenylmethane (2 g, 10.9 mmol) was added and the reaction mixture was heated at 65° C. After 3 h, the reaction mixture was cooled to room temperature and stirred for an additional 12 h. The resulting solid was filtered, washed with cold acetonitrile to give 1-benzyl-4-piperidylbenzhydryl carbamate (1.3 g, 50%) as a colorless solid which was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated at 65° C
  2. waitAfter 3 h
  3. temperaturethe reaction mixture was cooled to room temperature
  4. stirringstirred for an additional 12 h
  5. filtrationThe resulting solid was filtered
  6. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-3b2135b8eff44142a85591f1faa6c48e
Source dataset
uspto-grants-2008_11
Patent number
US07456203B2

Reaction notes

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