Trifluoroacetic acid → HCID 178444659, compound

HRID 428857Notes

Reaction equation

HRID 428857 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2([CH3:20])[CH:13]3[CH:9]2[CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12]3)[CH:5]=[CH:4][C:3]=1[NH2:21].[F:22][C:23]([F:28])([F:27])[C:24](O)=O>>[CH2:14]([N:11]1[CH2:10][CH:9]2[CH:13]([C:8]2([C:6]2[CH:5]=[CH:4][C:3]3[NH:21][C:24]([C:23]([F:28])([F:27])[F:22])=[N:1][C:2]=3[CH:7]=2)[CH3:20])[CH2:12]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22141195HCID 22141195, compound

Product 1

HCID 178444659HCID 178444659, compoundYield 54%

Procedure

A solution of 2-amino-4-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 48, 99.0 mg, 0.345 mmol) in trifluoroacetic acid (2.0 ml) was heated under reflux for 1 hour. The mixture was cooled and the solvent was removed in vacuo. The residue was suspended in 2N sodium hydroxide (5 ml) and the aqueous layer was extracted with diethyl ether (3×5 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography ieluting with ethyl acetate to afford the title compound (67 mg, 54%) as a colourless oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureThe mixture was cooled
  3. customthe solvent was removed in vacuo
  4. extractionthe aqueous layer was extracted with diethyl ether (3×5 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-3de144e3c55040f2a4b4146a75ad11ab
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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