Hydrochloric Acid → HCID 58495618, compound

HRID 1191025Notes

Reaction equation

HRID 1191025 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:14][CH:15]=1)=O)(C)(C)C.Cl>CO>[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59828835HCID 59828835, compound

Product 1

HCID 58495618HCID 58495618, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(tert-butoxycarbonylamino-methyl)-6-(piperidin-1-ylmethyl)-pyridine (540 mg, 1.76 mmol) in methanol (10 mL) and cool to 0° C. Bubble hydrogen chloride through the vigorously stirred solution for 30 min. Concentrate in vacuo. Partition the residue between 3N aqueous NaOH (10 mL) and DCM (20 mL). Separate the two layers and extract the aqueous layer with DCM (2×20 mL). Wash the combined organic extracts with brine (20 mL). Dry over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate as a colorless oil (351 mg, 95%). MS (APCI+) m/z: 206 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. customPartition the residue between 3N aqueous NaOH (10 mL) and DCM (20 mL)
  3. customSeparate the two layers
  4. extractionextract the aqueous layer with DCM (2×20 mL)
  5. washWash the combined organic extracts with brine (20 mL)
  6. dry with materialDry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f49713ca9cfc46ab92c26440f18becea
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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