Hydrochloric Acid → HCID 15662567, compound

HRID 1073431Notes

Reaction equation

HRID 1073431 reaction equation
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]([CH3:18])[CH2:16][CH3:17])=[CH:10][CH:9]=1)(C)[C:3]([NH2:5])=O.O.Cl>C1COCC1>[CH3:18][CH:15]([O:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:2]([CH3:1])[CH2:3][NH2:5])=[CH:9][CH:10]=1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131715274HCID 131715274, compound

Product 1

HCID 15662567HCID 15662567, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the above propanamide (1.32 g, 5.6 mmol) in 10 ml of THF at 0° is added dropwise 0.97 M BH3 -THF (35 ml) over 40 min. The solution is heated under reflux overnight and is then allowed to sit at RT for 48 hours, after which 10 ml of water is added dropwise over 30 min., followed by dropwise addition of 20 ml of aqueous 5N HCl. The THF is removed by distillation, and the aqueous phase is saturated with NaOH pellets and extracted with ether (3×). The combined organic layers are washed with water and with brine, dried and solvent removed to give 2-[4-(1-methylpropoxy)phenoxy]propylamine.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux overnight
  3. customThe THF is removed by distillation
  4. extractionextracted with ether (3×)
  5. washThe combined organic layers are washed with water and with brine
  6. customdried
  7. customsolvent removed

Sources & evidence

ORD record
ord-a2ad561fae3f4097bd5289714284933d
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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