Hydrochloric Acid → 1-(4-(Heptyloxy)phenyl)piperazin-2-one

HRID 716416Notes

Reaction equation

HRID 716416 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C:16]2=[O:28])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Cl.O1CCOCC1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][C:16]2=[O:28])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86689683Tert-butyl 4-(4-(heptyloxy)phenyl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 866896841-(4-(Heptyloxy)phenyl)piperazin-2-oneYield 81.1%

Procedure

To tert-butyl 4-(4-(heptyloxy)phenyl)-3-oxopiperazine-1-carboxylate (540 mg, 1.38 mmol) was added 4M HCl in dioxane (2.07 mL, 8.30 mmol). The reaction mixture was stirred at room temperature for 2 h. The precipitate was filtered, washed with hexane (5 mL) and dried. The crude product was purified by column chromatography (79/20/1 DCM/MeOH/NH4) to afford 325 mg (80%) of 1-(4-(heptyloxy)phenyl)piperazin-2-one as a colorless solid. LCMS-ESI (m/z) calculated for C17H26N2O2: 290.4. found 291.0 [M+H]+, tR=1.49 min. (Method 4).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with hexane (5 mL)
  3. customdried
  4. customThe crude product was purified by column chromatography (79/20/1 DCM/MeOH/NH4)

Sources & evidence

ORD record
ord-771143e805494af7b571a8cb5bed92b2
Source dataset
uspto-grants-2015_11
Patent number
US09187522B2

Reaction notes

Loading…