Tetrahydrofuran → [4-amino-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone

HRID 2247903Notes

Reaction equation

HRID 2247903 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:6][C:5]=1[CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)([O-])=O.S1C=CC=C1.O1CCCC1>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:6][C:5]=1[CH2:18][O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 8030ThiopheneHCID 15177085[4-nitro-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone

Product 1

HCID 19816012[4-amino-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanoneYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 20 parts of intermediate 56, namely [4-nitro-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl] phenylmethanone, 2 parts of a solution of thiophene in methanol 4% and 395 parts of methanol was hydrogenated overnight at normal pressure and room temperature with 2 parts of palladium-on-charcoal catalyst 10%. Tetrahydrofuran was added to dissolve the precipitated reaction product. The catalyst was filtered off and the filtrate was evaporated. The residue was recrystallized from methanol. The product was filtered off, washed with methanol and 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 14.93 parts (82.0%) of [4-amino-3-[[(tetrahydro-2H-pyran-2-yl)oxy]methy]phenyl] phenylmethanone; mp. 164.0° C. (interm. 57).

Workup

  1. dissolutionto dissolve
  2. customthe precipitated reaction product
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was recrystallized from methanol
  6. filtrationThe product was filtered off
  7. washwashed with methanol and 2,2'-oxybispropane
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-0360272be21c4f05b454f0f6fdc63bc7
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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