Pyridine → Ethyl 4-adamantan-1-yl-phenyl-carbamate

HRID 1900083Notes

Reaction equation

HRID 1900083 reaction equation
Cl.[C:2]12([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.N1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C(Cl)Cl>[C:2]12([C:12]3[CH:13]=[CH:14][C:15]([NH:18][C:26](=[O:27])[O:28][CH2:29][CH3:30])=[CH:16][CH:17]=3)[CH2:9][CH:8]3[CH2:10][CH:4]([CH2:5][CH:6]([CH2:7]3)[CH2:11]1)[CH2:3]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 27711374-(Adamantan-1-yl)aniline hydrochloride

Product 1

HCID 23371868Ethyl 4-adamantan-1-yl-phenyl-carbamateYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.28 g (20 mmol) of 4-adamantan-1-yl-phenylamine hydrochloride were placed in 100 ml of methylene chloride and treated with 3.22 g (42.0 mmol) of pyridine. A solution of 2.39 g (22.0 mmol) of ethyl chloroformate in 15 ml of methylene chloride was added dropwise to this suspension at room temperature while stirring during 15 minutes. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, the mixture was washed with water and the organic phase was dried over sodium sulfate, filtered and evaporated. The residue was recrystallized from methylene chloride/n-hexane. 5.6 g of ethyl 4-adamantan-1-yl-phenyl-carbamate were obtained as a white crystallizate. M.p.: 132°-134°.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. washSubsequently, the mixture was washed with water
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-97f07735c3b74d99829da0ac01f25c54
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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