Ammonium Chloride → 3-Amino-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 225047Notes

Reaction equation

HRID 225047 reaction equation
[Mg].[CH2:2]([O:4][CH2:5][CH2:6][CH2:7]Br)[CH3:3].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[CH:19]=[CH:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15](=[O:24])[C:14]=2[CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[CH:19]=[CH:18][C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[C:15]([CH2:7][CH2:6][CH2:5][O:4][CH2:2][CH3:3])([OH:24])[C:14]=2[CH:25]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2604931-bromo-3-ethoxypropaneHCID 5462224MagnesiumHCID 15628542HCID 15628542, compound

Product 1

HCID 233288763-Amino-5-(3-ethoxypropyl)-5H-dibenzo[a,d]cyclohepten-5-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium turnings (6.2 g., 0.255 mole) covered with dry tetrahydrofuran (30 ml.) in carefully-dried apparatus are treated with a solution of 3-ethoxypropylbromide (42.5 g., 0.255 mole) added dropwise to maintain reflux. After preparation of the Grignard reagent according to standard procedures, the mixture is cooled, and 16 g. (0.072 mole) of 3-amino-5H-dibenzo[a,d]cyclohepten-5-one added in portions over 5 minutes. The reaction is stirred 15 minutes, then poured into 200 ml. of saturated aqueous ammonium chloride. The layers are separated, and the aqueous layer extracted once with ether. The ether layer, combined with the original organic phase, is washed once with water, dried over sodium sulfate, and evaporated in vacuo to give the title compound in essentially quantitative yield.

Workup

  1. additionadded dropwise
  2. temperatureto maintain
  3. temperaturereflux
  4. temperaturethe mixture is cooled
  5. additionpoured into 200 ml
  6. customThe layers are separated
  7. extractionthe aqueous layer extracted once with ether
  8. washis washed once with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-872941dbf2144ede84b3f8f4f425ab9a
Source dataset
uspto-grants-1980_11
Patent number
US04235820

Reaction notes

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