Isoamyl Nitrite → HCID 86749046, compound

HRID 2210554Notes

Reaction equation

HRID 2210554 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[CH2:9][CH2:8]1)=[O:6].Cl.CCOCC.[N:34](OCCC(C)C)=[O:35]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:27])[C:4](=[N:34][OH:35])[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[CH:14]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 10953452Ether hydrochlorideHCID 54276370HCID 54276370, compound

Product 1

HCID 86749046HCID 86749046, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 3-[4-(3-cyclopentyloxy-4-methoxyphenyl)-piperidin-1-yl]-3-oxo-propionic acid methyl ester (5.3 mmol, 2.0 g) was added a solution of HCl/Et2O (1N, 55 mL) and isoamyl nitrite (6.36 mmol, 0.854 mL) at room temperature. After 10 minutes, the reaction mixture had become homogenous, and a white precipitate formed after and additional 30 minutes. After 3 hours, the reaction mixture was diluted with EtOAc and washed with H2O. The aqueous phase was extracted with EtOAc, the organics dried (Na2SO2) and concentrated in vacuo. The residue was triturated in Et2O/hexane to yield the title compound as a white solid, mp=159°-160° C. (4.7 mmol, 1.89 g, 88%).

Workup

  1. customa white precipitate formed after and additional 30 minutes
  2. waitAfter 3 hours
  3. washwashed with H2O
  4. extractionThe aqueous phase was extracted with EtOAc
  5. dry with materialthe organics dried (Na2SO2)
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in Et2O/hexane

Sources & evidence

ORD record
ord-fdc2384498914dd5845c5e2160972d91
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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