Formaldehyde → HCID 22414444, compound

HRID 486694Notes

Reaction equation

HRID 486694 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[N:10]([CH:12]=[O:13])[CH3:11].[CH2:20]=O.[C:22]([BH3-])#[N:23].[Na+]>C(#N)C>[CH3:20][N:23]([CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[N:10]([CH:12]=[O:13])[CH3:11]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 104234922-amino-N-formyl-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

Product 1

HCID 22414444HCID 22414444, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5.0 g of 2-amino-N-formyl-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine in 48 ml of acetonitrile was treated with 6.5 ml of a 37% formaldehyde solution and 1.9 g of sodium cyanoborohydride. The mixture was stirred for 1.5 hr and then concentrated. The residue was dissolved in 75 ml of ether and washed with 1N potassium hydroxide solution and with saturated brine. The ether solution was dried over anhydrous potassium carbonate and concentrated. The residue was purified by Preparative HPLC (Waters Associates Prep LC/System 500, silica gel, eluted with ethyl acetate, 200 ml/min, Glo-Mac Model 80-800 UV detector). The appropriate fractions were collected and concentrated to give 3.8 g of product, as an oil.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 75 ml of ether
  3. washwashed with 1N potassium hydroxide solution and with saturated brine
  4. dry with materialThe ether solution was dried over anhydrous potassium carbonate
  5. concentrationconcentrated
  6. customThe residue was purified by Preparative HPLC (Waters Associates Prep LC/System 500, silica gel, eluted with ethyl acetate, 200 ml/min, Glo-Mac Model 80-800 UV detector)
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-294537446c1e4d988af467a7ba545d11
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

Loading…