Ethanol → HCID 15860308, compound

HRID 1291707Notes

Reaction equation

HRID 1291707 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:12][C@H:11]1[CH2:13][NH2:14].FC1C=CC(OC)=CC=1[C@@H:24]1[CH2:26][C@H:25]1[C:27]#N.C(Cl)(Cl)Cl.CC[OH:35]>O=[Pt]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:12][C@H:11]1[CH2:13][NH:14][C:27](=[O:35])[CH:25]([CH3:24])[CH3:26]

Participants

6

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 53862340HCID 53862340, compoundHCID 53965268HCID 53965268, compound

Product 1

HCID 15860308HCID 15860308, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

(trans)-2-(2-Fluoro-5-methoxyphenyl)cyclopropanemethanamine: A suspension of (trans)-2-(2-fluoro-5-methoxyphenyl)cyclopropane carbonitrile (5.0 g, 26 mmol), PtO2 (200 mg), and CHCl3 (10 mL) in EtOH (65 mL) was hydrogenated in a Parr apparatus at 55 psi for 3 h. The catalyst was filtered through a plug of celite and the solvents were removed. The resulting hydrochloride salt was then partitioned between CH2Cl2 and 10% K2CO3. The organic layer was separated, dried over K2CO3, and concentrated to afford the title compound as the free amine, 3.8 g (74%): 1H NMR (250 MHz, CDCl3) δ0.79-0.82 (m, 1H), 0.90-0.95 (m, 1H), 1.49 (br s, 2H), 1.70-1.76 (m, 1H), 1.82-1.86 (m, 1H), 2.60-2.74 (m, 2H), 3.75 (s, 3H), 6.35-6.42 (m, 1H), 6.50-6.62 (m, 1H), 6.85-6.90 (m, 1H).

Workup

  1. filtrationThe catalyst was filtered through a plug of celite
  2. customthe solvents were removed
  3. customThe resulting hydrochloride salt was then partitioned between CH2Cl2 and 10% K2CO3
  4. customThe organic layer was separated
  5. dry with materialdried over K2CO3
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c577d4d0660f40258e0d86356753e10c
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Reaction notes

Loading…