Hydrochloric Acid → 5-Aminomethyl-2-(2-pyrrolidin-1-yl-ethoxy)-phenol

HRID 2236437Notes

Reaction equation

HRID 2236437 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:7]([OH:19])[CH:6]=1.Cl>C(O)C.[Pd]>[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:7]([OH:19])[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 722507613-Hydroxy-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde O-methyl-oxime

Product 1

HCID 592998755-Aminomethyl-2-(2-pyrrolidin-1-yl-ethoxy)-phenolYield 105.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 3-Hydroxy-4-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde O-methyl-oxime (50 mg, 0.18 mmol) is dissolved in ethanol (10 mL). Then hydrogen chloride (0.130 mL) is added, followed by 10% Pd/C (5.0 mg). After hydrogenation at 35 psi for 3 h, the solution is filtered through Celite and evaporated to dryness. The residue is recrystallized from ethyl acetate to give 45 mg of crude product as a white solid. MS (ESI) m/z 283.1 (M+1)

Workup

  1. filtrationthe solution is filtered through Celite
  2. customevaporated to dryness
  3. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-70fc5c51403d4a6980e4cbed23949ed9
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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