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

HRID 2058659Notes

Reaction equation

HRID 2058659 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 48h. 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 dissolved 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 48h
  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. dissolutionThe residue was dissolved in 60°-80° petrol (150 ml)
  8. customto crystallise

Sources & evidence

ORD record
ord-b49026996681496e82e3bf5a20012a84
Source dataset
uspto-grants-1982_03
Patent number
US04318909

Reaction notes

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