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

HRID 2058661Notes

Reaction equation

HRID 2058661 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 12h the mixture was filtered, and 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. (Found: C, 66.1; H, 6.2; N, 4.1%; C17H19ClFNO requires: C, 66.3; H, 6.2; N, 4.55%).

Workup

  1. filtrationAfter 12h the mixture was filtered
  2. customfiltrate evaporated
  3. customthe residue chromatographed on silica (Woelm Grade 1)

Sources & evidence

ORD record
ord-588a8b1336a541ee860dcc8dddfc9a32
Source dataset
uspto-grants-1982_03
Patent number
US04318909

Reaction notes

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