Iodoethane → HCID 68828674, compound

HRID 1784407Notes

Reaction equation

HRID 1784407 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.[H-].[Na+].[CH2:22](I)[CH3:23]>CN(C)C=O.C(OCC)C.O>[CH2:22]([O:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1)[CH3:23]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18173274tert-butyl 7-hydroxy-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

Product 1

HCID 68828674HCID 68828674, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxy-3-(t-butoxycarbonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (10 g, 38 mmol) in dimethylformamide (70 mL) was added sodium hydride (60% dispersion in oil, 1.5 g) and the resulting mixture stirred for 0.5 h. Ethyl iodide (3.6 mL, 45 mmol) was added and the mixture stirred for 12 h at 70° C. The mixture was cooled to room temperature and diluted with diethyl ether (200 mL) and water (200 mL), the layers were separated and the aqueous portion extracted with diethyl ether (200 mL). The combined organic extracts were washed with brine (200 mL) and sodium hydroxide solution (2N, 200 mL) and then evaporated to give a yellow oil.

Workup

  1. stirringthe mixture stirred for 12 h at 70° C
  2. customthe layers were separated
  3. extractionthe aqueous portion extracted with diethyl ether (200 mL)
  4. washThe combined organic extracts were washed with brine (200 mL) and sodium hydroxide solution (2N, 200 mL)
  5. customevaporated
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-960e7ac0b2c94956a40d2aa634ceda51
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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