Ammonia → HCID 54552279, compound

HRID 1755813Notes

Reaction equation

HRID 1755813 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH2:11])[CH3:10])=[CH:5][CH:4]=1.C(O)(C)(C)C.N.[Li]>C1COCC1.C(O)C>[NH2:11][C@H:9]([C:6]1[CH2:7][CH:8]=[C:3]([O:2][CH3:1])[CH2:4][CH:5]=1)[CH3:10]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 6386tert-ButanolHCID 793467(S)-1-(4-Methoxyphenyl)ethylamineHCID 3028194Lithium

Product 1

HCID 54552279HCID 54552279, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mechanically stirred solution of the above amine (30) (24 g) in dry THF (200 mL) and t-butanol (12 g) was condensed via a cold finger ammonia (800 mL). Lithium wire (3.1 g) was next added piece-wise over 15 min and the now dark blue reaction stirred for 1 h. Ethanol was then dripped into the reaction very slowly over 1 h until the reaction turned blue. The reaction was then allowed to warm to room temperature, with external warming, to allow the ammonia to evaporate. The remaining mixture was taken up in ethyl ether, washed with H2O, dried over Na2SO4 and evaporated to yield the titled product (31): GC RT 5.63 min (HP 530 mμ×20 m methylsilicone colunm, He carrier flow rate 20 mL/min, 100° C. isothermal).

Workup

  1. customover 15 min
  2. customthe now dark blue reaction
  3. customto evaporate
  4. washwashed with H2O
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-90250c66d4864f9aa27ef044e40f71b8
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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