2,2,6,6-Tetramethylpiperidine → N-(2-fluorophenylmethyl)-3-hydroxy-N-methyl-3-phenylpropylamine

HRID 1248794Notes

Reaction equation

HRID 1248794 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[F:10].Cl[CH2:12][CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15].CC1(C)CCCC(C)(C)N1>C(#N)C>[F:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:2]([CH2:12][CH2:13][CH:14]([OH:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:1]

Participants

5

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 5720643-Chloro-1-phenylpropanolHCID 20608422-Fluoro-N-methylbenzylamine

Product 1

HCID 12951843N-(2-fluorophenylmethyl)-3-hydroxy-N-methyl-3-phenylpropylamineYield 59.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-methyl-o-fluorobenzylamine (27.8 g), 3-chloro-1-phenylpropan-1-ol(34.2 g), 2,2,6,6-tetramethylpiperidine (34.4 ml) and acetonitrile (500 ml) was refluxed for 48 h. The mixture was cooled to room temperature, filtered and the solvent removed. The residue was partitioned between chloroform and aqueous sodium bicarbonate. The organic phase was dried and the solvent removed. The residue was disolved in 60°-80° petrol (150 ml) and allowed to crystallise yielding the title compound (32.4 g) which is cyclodehydrohalogenated as in Example 4.

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationfiltered
  3. customthe solvent removed
  4. customThe residue was partitioned between chloroform and aqueous sodium bicarbonate
  5. customThe organic phase was dried
  6. customthe solvent removed
  7. customwas disolved in 60°-80°
  8. customto crystallise

Sources & evidence

ORD record
ord-2e5453821c97437ca618ec969d7a2941
Source dataset
uspto-grants-1986_12
Patent number
US04626522

Reaction notes

Loading…