2,2,6,6-Tetramethylpiperidine → HCID 12951849, compound

HRID 1248796Notes

Reaction equation

HRID 1248796 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7]Br.[CH3:11][NH:12][CH2:13][CH2:14][CH:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC1(C)CCCC(C)(C)N1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH2:7][N:12]([CH2:13][CH2:14][CH:15]([OH:22])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:11])[CH:9]=1

Participants

5

Reactant 3

HCID 130352,2,6,6-TetramethylpiperidineHCID 27339893-Methylamino-1-phenylpropanolHCID 27736262-(Bromomethyl)-4-chloro-1-fluorobenzene

Product 1

HCID 12951849HCID 12951849, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5-chloro-2-fluorobenzyl bromide (10.5 g) in acetonitrile (100 ml) was added dropwise to a mixture of N-methyl-3-hydroxy-3-phenylpropylamine (7.7 g), 2,2,6,6-tetramethylpiperidine (8 ml) and acetonitrile (100 ml) After 12 h the mixture was filtered, the filtrate evaporated and the residue chromatographed on silica (Woelm Grade 1) using ether as eluant to give the title compound as an oil (10.5 g), b.p. 160°/0.5 mm.

Workup

  1. filtrationwas filtered
  2. customthe filtrate evaporated
  3. customthe residue chromatographed on silica (Woelm Grade 1)

Sources & evidence

ORD record
ord-5af6250c11304b38834468bb30d787f9
Source dataset
uspto-grants-1986_12
Patent number
US04626522

Reaction notes

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