Cyclopentylamine → HCID 86717740, compound

HRID 2271329Notes

Reaction equation

HRID 2271329 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]1([NH2:21])[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][NH:21][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 86717739HCID 86717739, compound

Product 1

HCID 86717740HCID 86717740, compoundYield 87.5%

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 cyclopentylamine (1.34 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 (443 mg, 87.4%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 207.5° C. MS m/z (relative intensity, 70 eV) 301(M+, 2), 272 (7), 99 (24), 98 (bp), 70 (7).

Workup

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

Sources & evidence

ORD record
ord-3bd21945be9448d69602088c0f79a153
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

Loading…