Formic Acid → HCID 178444660, compound

HRID 428856Notes

Reaction equation

HRID 428856 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].[OH-].[Na+].[CH:24](O)=O>O>[NH3:1].[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][CH:24]=[N:1][C:2]=3[CH:7]=2)[CH3:20])[CH2:12]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 22141195HCID 22141195, compound

Product 2

HCID 222AmmoniaHCID 178444660HCID 178444660, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-amino-4-(3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenylamine (Preparation 48, 112 mg, 0.39 mmol) in formic acid (2.0 ml) was heated under reflux for 1 h. The mixture was cooled, diluted with water (3 ml) and the pH adjusted to 10 with 5N sodium hydroxide. The aqueous layer was extracted with diethyl ether (3×5 ml) and ethyl acetate (2×5 ml). The combined organic layers were dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was purified by silica columnn chromatography eluting with ethyl acetate then ethyl acetate:methanol:ammonia solution (0.880) (80:20:1) to afford the title compound (46 mg, 40%) as a colourless oil.

Workup

  1. temperatureunder reflux for 1 h
  2. temperatureThe mixture was cooled
  3. extractionThe aqueous layer was extracted with diethyl ether (3×5 ml) and ethyl acetate (2×5 ml)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe crude residue was purified by silica columnn chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-aa49aa18141a4095b3d8fec2b2fb9b75
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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