HCID 15388860, compound → HCID 15388861, compound

HRID 1900251Notes

Reaction equation

HRID 1900251 reaction equation
[CH2:1]([O:3][CH:4]([CH:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2)[C:5]([N:7]([CH3:9])[CH3:8])=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:3][CH:4]([CH:10]1[C:11]2[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=2[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2)[CH2:5][N:7]([CH3:9])[CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 15388860HCID 15388860, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15388861HCID 15388861, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Dissolved 2-ethoxy-2-[10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl]-N,N-dimethyl-acetamide (4.45 g, 13.8 mmol) in 100 mL of dry tetrahydrofuran, and added lithium aluminum hydride (0.6 g, 15.8 mmol) portionwise under a nitrogen atmosphere. Heated the reaction mixture at 60° C. for 2 hours. Cooled to 0° C., and carefully added 0.6 mL of water, 0.6 mL of 15 weight % NaOH, and then 1.8 mL of water in order to precipitate aluminum salts. Filtered precipitate, and washed with tetrahydrofuran. Evaporated filtrate, and purified the crude product by flash chromatography on silica gel eluting with 1:1 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 3.44 g (81% yield) of β-ethoxy-10,11-dihydro-N, N-dimethyl-5 H-dibenzo[a,d]cycloheptene-5-ethanamine as a colorless oil. Dissolved free base in ethyl acetate, and added one equivalent of maleic acid dissolved in methanol. Evaporated, and added ether to precipitate maleate salt.

Workup

  1. temperatureCooled to 0° C.
  2. customcarefully added 0.6 mL of water, 0.6 mL of 15 weight % NaOH, and then 1.8 mL of water in order to precipitate aluminum salts
  3. filtrationFiltered precipitate
  4. washwashed with tetrahydrofuran
  5. customEvaporated filtrate, and purified the crude product by flash chromatography on silica gel eluting with 1:1 ethyl acetate
  6. customevaporated

Sources & evidence

ORD record
ord-408bf372734b4d4d82013caf1e8a4ff6
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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