Formaldehyde → HCID 67049837, compound

HRID 885843Notes

Reaction equation

HRID 885843 reaction equation
[ClH:1].[CH3:2][C@H:3]1[NH:8][C@@H:7]([CH3:9])[CH2:6][N:5]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:4]1.[BH3-][C:19]#N.[Na+].C=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[ClH:1].[CH3:9][C@H:7]1[N:8]([CH3:19])[C@@H:3]([CH3:2])[CH2:4][N:5]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6]1

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride2×HCID 67049435HCID 67049435, compound

Product 1

HCID 67049837HCID 67049837, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-benzonitrile hydrochloride (1 g, 3.97 mmol) was dissolved in DCM (25 ml) and TEA (1.1 ml, 7.94 mmol). NaBH3CN (374 mg, 5.96 mmol) and CH2O (37% water solution, 0.446 ml, 5.96 mmol) were added to the resulting solution. The slurry was stirred overnight at room temperature, then further CH2O (0.297 ml, 3.97 mmol) and NaBH3CN (249 mg, 3.97 mmol) were added. The slurry was stirred at room temperature for 4 h, then brought to basic conditions with 5% NaHCO3 and extracted twice with DCM. The collected organic phases were dried over Na2SO4 and evaporated in vacuo. The resulting oil was taken up with DCM and treated with HCl/Et2O. The precipitate was filtered and washed with di-isopropylether to give 1 g of 4-((3R,5S)-3,4,5-trimethyl-piperazin-1-yl)-benzonitrile hydrochloride.

Workup

  1. stirringThe slurry was stirred at room temperature for 4 h
  2. extractionextracted twice with DCM
  3. dry with materialThe collected organic phases were dried over Na2SO4
  4. customevaporated in vacuo
  5. additiontreated with HCl/Et2O
  6. filtrationThe precipitate was filtered
  7. washwashed with di-isopropylether

Sources & evidence

ORD record
ord-b42ae0a245b94552a477a144e56f36f6
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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