Piperidine → HCID 70979664, compound

HRID 2271333Notes

Reaction equation

HRID 2271333 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=[C:7]([F:15])[CH:6]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(O)C>[F:15][C:7]1[CH:6]=[C:5]([CH:10]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:8]=1)[O:4][CH2:3][CH2:2][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86717739HCID 86717739, compound

Product 1

HCID 70979664HCID 70979664, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation according to Example 1 but performed in one portion: 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.68 mmol) and piperidine (1.33 ml, 13.46 mmol) in ethanol (5 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (480 mg, 94.7%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 194.6° C. MS m/z (relative intensity, 70 eV) 301(M+, 1), 99 (8), 98 (bp), 96 (4), 55 (5).

Workup

  1. customPreparation
  2. customPurification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15)

Sources & evidence

ORD record
ord-8260de044b534d959a9cee3933eca8a6
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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