Hydrochloric Acid → HCID 22622517, compound

HRID 840318Notes

Reaction equation

HRID 840318 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:6]([CH:9]=1)[CH:7]=O.Cl.[CH2:17]([NH2:19])[CH3:18].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO.C(O)(=O)C>[CH2:17]([NH:19][CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22622522187241-82-3

Product 1

HCID 22622517HCID 22622517, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-2-cyclopentoxybenzaldehyde (9.35 g, 41.6 mmol) and ethylamine hydrochloride (18.6 g, 229 mmol) in methanol (100 ml) for 30 minutes at ambient temperatures, following which sodium cyanoborohydride (5.6 g, 88 mmol) was added and the reaction left to reflux at 70 ° C. for 70 hours with periodic acidification to pH 6 using glacial acetic acid. Normal hydrochloric acid (100 ml) was added in a dropwise fashion and the resultant mixture basified with 2 normal sodium hydroxide solution until a pH of 11 existed, whereupon the product was extracted into dichloromethane (250 ml×2) and ethyl acetate (250 ml×2). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and the solvent removed to yield the title compound (8.5 g, 80%).

Workup

  1. additionwas added
  2. waitthe reaction left
  3. extractionwas extracted into dichloromethane (250 ml×2) and ethyl acetate (250 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-25ffc25fd9d24718b7fa2a55ac146f9c
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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