HCID 86718003, compound → 5-Methyl-4-(piperidin-4-yl)-2,3-dihydrobenzofuran-7-amine

HRID 1500465Notes

Reaction equation

HRID 1500465 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1>CC(O)=O.O=[Pt]=O>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:17])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 86718003HCID 86718003, compound

Product 1

HCID 867180045-Methyl-4-(piperidin-4-yl)-2,3-dihydrobenzofuran-7-amine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 5-methyl-4-(pyridin-4-yl)-2,3-dihydrobenzofuran-7-amine (1f) (0.40 g, 1.8 mmol), PtO2 (120 mg, 35%) and TEA (0.24 mL, 3.6 mmol) in HOAc (30 mL) was introduced H2 and stirred at ambient temperature for 24 h (88 psi). The mixture was filtered, concentrated, diluted with EtOAc (50 mL). A solution of ammonium hydroxide was added until pH=10, it was extracted with EtOAc (150 mL), washed with water, brine, dried and concentrated to give the title compound (1g) as a yellow oil. MS-ESI (m/z): 233 (M+1)+.

Workup

  1. additionwas introduced H2
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated
  4. additiondiluted with EtOAc (50 mL)
  5. additionA solution of ammonium hydroxide was added until pH=10, it
  6. extractionwas extracted with EtOAc (150 mL)
  7. washwashed with water, brine
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a039c44a4d53451a97fa68c47c5516e2
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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