Aniline → N-phenyladamantan-1-amine

HRID 617133

Reaction equation

HRID 617133 reaction equation
Br[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCCCCC>C(OCC)(=O)C>[C:2]12([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

5

Reactant 3

HCID 6115AnilineHCID 8058HexaneHCID 791061-Bromoadamantane

Product 1

HCID 303939N-phenyladamantan-1-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

Under a nitrogen (N2) atmosphere was combined 10.0 g (46.5 mmol) of 1-bromoadamantane and 20 ml of aniline. The reaction was stirred for 20 hours at 200° C., and then cooled and fractionated on silica gel using 6:1 hexane:ethyl acetate (EtOAc) to afford, after concentration in vacuo and refractionation using toluene, 5.65 g (54%) of N-1-adamantylaniline.

Workup

  1. temperaturecooled
  2. concentrationafter concentration in vacuo and refractionation

Sources & evidence

ORD record
ord-b55a2f58a31a42d9b38ecbebfa45ab7a
Source dataset
uspto-grants-1999_09
Patent number
US05948781

Linked notes

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