Hydrochloric Acid → [1-Azetidin-3-yl-4-(phenylcarbonyl)piperazin-2-yl]methanol

HRID 2365644Notes

Reaction equation

HRID 2365644 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:19])[CH2:14][CH:13]3[CH2:26][OH:27])[CH2:9]2)C=CC=CC=1.Cl>CCO>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[CH2:14][CH:13]2[CH2:26][OH:27])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59625708{1-[1-(Diphenylmethyl)azetidin-3-yl]-4-(phenylcarbonyl)piperazin-2-yl}methanol

Product 1

HCID 59625928[1-Azetidin-3-yl-4-(phenylcarbonyl)piperazin-2-yl]methanolYield 152.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 37e (450 mg, 1.02 mmol) was added to a 500 mL-Parr hydrogenation bottle and dissolved in absolute EtOH (6 mL). A 12N conc. HCl solution (95 μL, 1.14 mmol) was added and the bottle was purged with N2. 10% Pd/C (264 mg) was added and the mixture was shaken under 60 psi of H2 for 14 h. An additional amount of 10% Pd/C (430 mg) was added and the mixture was returned to 60 psi of H2 and shaken 5 h more. The mixture was filtered through a pad of diatomaceous earth, and the solids were rinsed thoroughly with MeOH. The Titrate was concentrated to dryness under reduced pressure to afford crude compound 37f as a sticky oil (428 mg) which was used in the following step without further purification. LC/MS m/z (M+H+) 276.3.

Workup

  1. customthe bottle was purged with N2
  2. addition10% Pd/C (264 mg) was added
  3. additionAn additional amount of 10% Pd/C (430 mg) was added
  4. stirringshaken 5 h more
  5. filtrationThe mixture was filtered through a pad of diatomaceous earth
  6. washthe solids were rinsed thoroughly with MeOH
  7. concentrationThe Titrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bcee3baf13a84dfc9e7c7fce2d4cb397
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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