Lithium → HCID 21896896, compound

HRID 719127Notes

Reaction equation

HRID 719127 reaction equation
CO[N:3]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH:5]([NH2:12])[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Li]>C(OCC)C>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([CH:4]([NH2:3])[CH:5]([NH2:12])[CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 738525462-amino-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime

Product 1

HCID 21896896HCID 21896896, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-amino-1-(4-chloro-phenyl)-3-cyclopentyl-propan-1-one O-methyl-oxime (420 mg, 1.567 mmol) in diethyl ether (3 mL) was added dropwise to a slurry mixture of lithium aluminumhydride (307 mg, 7.835 mmol) in diethyl ether (30 mL) cooled to 0° C. At the end of addition, the icebath was removed and the reaction was stirred at room temperature for 3 h. The reaction mixture was cooled to 0° C. and aqueous solution of sodium chloride was added to quench the excess lithium aluminumhydride. Sodium hydroxide solution was added and the biphasic mixture was stirred for 1 h. The product was extracted with diethyl ether (3×30 mL). The ethereal extracts were washed with brine and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 1-(4-chloro-phenyl)-3-cyclopentyl-propane-1,2-diamine as yellow oil (362.7 mg, 96%, 4.3:1.0 ratio of cis:trans). The crude product was used without further purification.

Workup

  1. additionAt the end of addition
  2. customthe icebath was removed
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. additionaqueous solution of sodium chloride was added
  5. customto quench the excess lithium aluminumhydride
  6. additionSodium hydroxide solution was added
  7. stirringthe biphasic mixture was stirred for 1 h
  8. extractionThe product was extracted with diethyl ether (3×30 mL)
  9. washThe ethereal extracts were washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customEvaporation of the solvent

Sources & evidence

ORD record
ord-3054e6448ed4458fa0ba4a3acb7e21d6
Source dataset
uspto-grants-2006_11
Patent number
US07132421B2

Reaction notes

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