1-Biphenyl-2-ylmethanamine → HCID 86593358, compound

HRID 1823801Notes

Reaction equation

HRID 1823801 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(Cl)=[O:16].C1(C)C=CC=CC=1.[C@@:26]12([OH:35])[N:33]([CH3:34])[C@@H:30]([CH2:31][CH2:32]1)[CH2:29][CH:28]=[CH:27]2>C(=O)(O)[O-].[Na+].ClCCl.C(#N)C>[C:8]1([CH2:9][NH:10][C:15]([O:35][C@@:26]23[N:33]([CH3:34])[C@@H:30]([CH2:31][CH2:32]2)[CH2:29][CH:28]=[CH:27]3)=[O:16])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 2633661-Biphenyl-2-ylmethanamineHCID 19083224Phosgen tolueneHCID 53629842Tropenol

Product 1

HCID 86593358HCID 86593358, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

3.67 g (0.02 mol) of 2-phenylbenzylamine is placed in 250 mL saturated sodium bicarbonate solution and 250 mL dichloromethane. At 0° C., 52.9 mL (0.10 mol) of 20% phosgene-toluene solution are added under the surface of the dichloromethane. The mixture is vigorously stirred for 30 minutes. The two phases are separated, the organic phase is dried over sodium sulfate and evaporated to dryness. The residue is dissolved in 20 mL acetonitrile and 4.18 g (0.03 mol) of tropenol in 10 mL acetonitrile is added dropwise, whereupon a precipitate is formed. It is stirred for 12 hours at ambient temperature. The precipitate is suction filtered and the mother liquor evaporated to dryness. The residue is dissolved in dichloromethane and washed with water, water mixed with acetic acid (2 drops of glacial acetic acid to 100 mL of water), and 10% sodium carbonate solution. The organic phase is dried and evaporated to dryness. Yield: 2.85 g (41% of theory).

Workup

  1. customThe two phases are separated
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customevaporated to dryness
  4. dissolutionThe residue is dissolved in 20 mL acetonitrile
  5. customis formed
  6. stirringIt is stirred for 12 hours at ambient temperature
  7. filtrationfiltered
  8. customthe mother liquor evaporated to dryness
  9. dissolutionThe residue is dissolved in dichloromethane
  10. washwashed with water, water
  11. additionmixed with acetic acid (2 drops of glacial acetic acid to 100 mL of water), and 10% sodium carbonate solution
  12. customThe organic phase is dried
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-1a2fe01324ed473c974e8bc953ebef60
Source dataset
uspto-grants-2006_05
Patent number
US07041674B2

Reaction notes

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