Hydrochloric Acid → HCID 18617570, compound

HRID 1264321Notes

Reaction equation

HRID 1264321 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[CH3:17][NH:18][CH3:19].[BH3-]C#N.[Na+].Cl>CO>[CH3:17][N:18]([CH3:19])[CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10473Dimethylamine, hydrochlorideHCID 5003444Sodium cyanoborohydride2×HCID 110198874-(4-Oxopiperidin-1-yl)benzonitrile

Product 1

HCID 18617570HCID 18617570, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-oxo-piperidin-1-yl)-benzonitrile (100 mg, 0.5 mmol, reference example 116) dimethylamine hydrochloride (408 mg, 5 mmol) and NaCNBH3 (25 mg, 0.4 mmol) was dissolved in MeOH (7 mL) and stirred at room temperature overnight. After 24 h, additional NaCNBH3 (24 mg, 0.38 mmol) was added and the mixture was stirred overnight at room temperature. The pH of the mixture was adjusted to pH 2 with concentrated HCl and extracted with Et2O (3×). The aqueous phase was adjusted to pH 10 with KOH pellets, and extracted (3×) with Et2O. The latter combined organic phases were washed with brine, dried with Na2SO4, filtered and evaporated. The crude material was taken into the next step without further purification. 1H NMR (CDCl3): δ 7.44 (d, 2H), 6.83 (d, 2H), 3.86 (m, 2H), 2.86 (dt, 2H), 2.32-2.38 (m, 1H), 2.28 (s, 6H), 1.92 m(m, 2H), 1.54 (dq, 2H). MS (EI) m/z 229 (M+H)+.

Workup

  1. waitAfter 24 h
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionextracted with Et2O (3×)
  4. extractionextracted (3×) with Et2O
  5. washThe latter combined organic phases were washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude material was taken into the next step without further purification

Sources & evidence

ORD record
ord-3e5c096a7c15400f8052fa3abcb38253
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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