Propylamine → HCID 44481360, compound

HRID 452399Notes

Reaction equation

HRID 452399 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[CH2:5][O:4]1.[CH2:20]([NH2:23])[CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:17][C:16]([F:19])([F:18])[S:13]([C:10]1[CH:11]=[CH:12][C:6]2[CH2:5][O:4][CH:3]([CH2:2][NH:23][CH2:20][CH2:21][CH3:22])[O:8][C:7]=2[CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 11430Potassium CarbonateHCID 67155666HCID 67155666, compound

Product 1

HCID 44481360HCID 44481360, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(bromomethyl)-7-[(trifluoromethyl)sulfonyl]-4H-1,3-benzodioxine (1.0 g, 2.77 mmol), propan-1-amine (2.27 ml, 27.7 mmol), potassiumcarbonate (0.57 g, 4.15 mmol) and ACN were heated at 60° C. for 16 h. The volatiles were evaporated and the crude product was purified by flash column chromatography using EtOAc/MeOH (10:1) as eluent, to afford the title product (0.55 g, 58%). The amine (0.30 g) was converted into the hydrochloric acid salt and crystallized from EtOH/DEE. M.p. 201° C. MS m/z (rel. intensity, 70 eV) 339 (M+, 5), 310 (22), 239 (18), 222 (8), 72 (bp).

Workup

  1. customThe volatiles were evaporated
  2. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-e5e29c10d1d440bf8daf7b6d004a3a74
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

Loading…