Ammonium Chloride → HCID 28945761, compound

HRID 576988Notes

Reaction equation

HRID 576988 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH3:17])[CH2:12][CH2:11]2)[C:3]=1[CH:4]=[O:5].[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH2:15]2)[C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 28603767HCID 28603767, compound

Product 1

HCID 28945761HCID 28945761, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2-chloro-6-(4-ethylpiperazin-1-yl)benzaldehyde (7.4 g, 29.4 mmol) in anhydrous methanol (150 mL) was added sodium borohydride (1.7 g, 44 mmol). The reaction mixture was stirred at 0° C. for 0.5 hour and at room temperature overnight. After cooling to 0° C., a saturated ammonium chloride solution (200 mL) was added. The resultant mixture was extracted with DCM (3×100 mL) and EtOAc (1×100 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording [2-chloro-6-(4-ethylpiperazin-1-yl)phenyl]methanol (6.3 g, 84% yield). The product was used without further purification.

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionThe resultant mixture was extracted with DCM (3×100 mL) and EtOAc (1×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-17938f4e546a4d9a8164df8a341fd8fd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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