Hydrochloric Acid → (3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine hcl

HRID 7212Notes

Reaction equation

HRID 7212 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([CH3:14])[C@H:10]([NH:15][CH3:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:17]>C(O)C>[ClH:17].[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([CH3:14])[C@H:10]([NH:15][CH3:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 44630605(3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine

Product 1

HCID 67009901(3S,4S)-1-Benzyl-N,4-dimethylpiperidin-3-amine hclYield 37.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The final salt formation was performed by charging 1.5 grams cis-(1-benzyl-4-methyl-piperidin-3-yl)-methyl-amine (1 equiv., 5.15 mmol) and 4.5 ml ethanol (3 volumes) to a reactor at 0° C. To the 0° C. pot, was charged 0.93 ml 36% HCl (0.625 volumes) so that the temperature stayed below 10° C. Next 3 mis ethanol (2 volumes) were concentrated from the reaction. To the reaction was charged 7.5 mls ethyl acetate (5 volumes), the reaction was stirred for 5 minutes and then 6 mls ethyl acetate (4 volumes) were removed in vacuo. 7.5 mls ethyl acetate (5 volumes) were again charged and the concentration was again performed. Next, 4.5 mls acetone (3 volumes) were added and the reaction was slowly cooled to 0° C. in order to afford white solids. (37.5% yield). 1H NMR: δ7.78-7.76 (2 H, d, J=8.0 Hz), 7.29-7.18 (5 H, m, aromatic protons), 5.55 (1 H, s), 3.45-3.41 (1 H, d, J=13.2 Hz), 3.39-3.36 (1 H, d, J=13.2 Hz), 2.79 (1 H, brs), 2.63 (1 H, brs), 2.45 (3 H, s), 2.30 (2 H, s), 2.25-2.05 (1H, m), 1.76 (1 H, brs), 1.40-1.39 (2 H, m), 0.875-0.845 (3 H, d, J=12).

Workup

  1. customat 0° C
  2. customstayed below 10° C
  3. concentrationNext 3 mis ethanol (2 volumes) were concentrated from the reaction
  4. additionTo the reaction was charged 7.5 mls ethyl acetate (5 volumes)
  5. custom6 mls ethyl acetate (4 volumes) were removed in vacuo
  6. addition7.5 mls ethyl acetate (5 volumes) were again charged
  7. concentrationthe concentration
  8. additionNext, 4.5 mls acetone (3 volumes) were added
  9. customto afford white solids

Sources & evidence

ORD record
ord-6580e1657d6048b4bad2318e49008042
Source dataset
uspto-grants-2006_08
Patent number
US07084277B2

Reaction notes

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