Sec-Butylamine → HCID 70979358, compound

HRID 2271328Notes

Reaction equation

HRID 2271328 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.[CH:16]([NH2:20])([CH2:18][CH3:19])[CH3:17]>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][NH:20][CH:16]([CH2:18][CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 86717739HCID 86717739, compound

Product 1

HCID 70979358HCID 70979358, compoundYield 70.4%

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 sec-butylamine 1.37 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 (342 mg, 70%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 166.5° C. MS m/z (relative intensity, 70 eV) 289 (M+, 1), 261 (25), 260 (bp), 86 (49), 70 (12).

Workup

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

Sources & evidence

ORD record
ord-cf9ae5bd8cd641afb02f1ffd3ef819eb
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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