HCID 67309471, compound → HCID 67310805, compound

HRID 2061072Notes

Reaction equation

HRID 2061072 reaction equation
[Cl-:1].C(OC([NH:12][C:13]([CH3:26])([CH3:25])[CH2:14][CH2:15][N+:16]1([CH3:24])[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18][CH2:17]1)=O)C1C=CC=CC=1>[Pd].O>[ClH:1].[Cl-:1].[NH2:12][C:13]([CH3:26])([CH3:25])[CH2:14][CH2:15][N+:16]1([CH3:24])[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 67309471HCID 67309471, compound

Product 1

HCID 67310805HCID 67310805, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

1-(3-(Benzyloxycarbonylamino)-3-methylbutyl)-4,4-difluoro-1-methylpiperidinium chloride (1.78 g, 4.49 mmol) was dissolved into water (100 mL) and 10% Pd/C (300 mg) was added to the flask. It was sealed and degassed with vacuum and flushed with hydrogen from a balloon (3 times). The reaction was stirred at room temperature for 17 h. The suspension was filtered through a pad of Celite® and the solid was washed with water (2×50 mL). The filtrate was concentrated to a viscous oil which became a white foam after being dried under high vacuum (1.30 g, quant). LRMS (ESI+) for C11H23F2N2+ (221.1); Found: 221 (M+).

Workup

  1. additionwas added to the flask
  2. customIt was sealed
  3. customdegassed with vacuum
  4. customflushed with hydrogen from a balloon (3 times)
  5. filtrationThe suspension was filtered through a pad of Celite®
  6. washthe solid was washed with water (2×50 mL)
  7. concentrationThe filtrate was concentrated to a viscous oil which
  8. customafter being dried under high vacuum (1.30 g, quant)

Sources & evidence

ORD record
ord-a0c8fcbcdde348c4bbfa0d33c1d20c6d
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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