Formaldehyde → Ammonia

HRID 2054698Notes

Reaction equation

HRID 2054698 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][C@@H:15]2[CH2:17][C@H:12]1[CH2:13][NH:14]2.[CH2:18]=O>C(O)=O>[NH3:1].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:16][C@@H:15]2[CH2:17][C@H:12]1[CH2:13][N:14]2[CH3:18]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 16747864HCID 16747864, compound

Product 2

HCID 222AmmoniaHCID 69211650HCID 69211650, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2-(2-quinolinyl)-(1S,4S)-2,5-diazabicyclo-[2.2.1]-heptane (0.39 g; 1.73 mmol), formaldehyde (2 ml; 37%) and formic acid (2 ml) was stirred at reflux for 24 hours. The solvent was evaporated. Aqueous sodium hydroxide (50 ml; 1 M) was added, followed by extraction with diethyl ether (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.35 g (85%).

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent was evaporated
  3. additionAqueous sodium hydroxide (50 ml; 1 M) was added
  4. extractionfollowed by extraction with diethyl ether (3×50 ml)

Sources & evidence

ORD record
ord-5e9228656b594a3691e9aae9251e4e7f
Source dataset
uspto-grants-2008_02
Patent number
US07329754B2

Reaction notes

Loading…