Hydrochloric Acid → HCID 15749400, compound

HRID 1196992Notes

Reaction equation

HRID 1196992 reaction equation
[Mg].[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6]Cl.[O:9]=[C:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][O:13][C:12]2[CH:21]=[CH:22][C:23]([CH2:25][CH2:26][O:27][C:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:24][C:11]1=2.[Cl-].[NH4+].Cl>O1CCCC1.BrC(Br)C>[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6][C:10]1([OH:9])[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][O:13][C:12]2[CH:21]=[CH:22][C:23]([CH2:25][CH2:26][O:27][C:28]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:24][C:11]1=2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 5462224MagnesiumHCID 1412718711-Oxo-2-(2-triphenylmethyloxyethyl)-6,11-dihydrodibenz[b,e]oxepin

Product 1

HCID 15749400HCID 15749400, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-dimethylaminopropyl magnesium chloride obtained by reacting 0.2 g of magnesium with 1.0 g of 3-dimethylaminopropyl chloride in 10 ml of tetrahydrofuran under a nitrogen atmosphere using dibromoethane as a catalyst, is dropwise added a solution obtained by dissolving 2.0 g of 11-oxo-2-(2-triphenylmethyloxyethyl)-6,11-dihydrodibenz[b,e]oxepin in 10 ml of tetrahydrofuran under ice cooling and the mixture is stirred at room temperature for one day. Aqueous ammonium chloride solution is added thereto and the pH of the mixture is adjusted to 7.0 with aqueous 4N-hydrochloric acid solution. The solvent is distilled away under reduced pressure. The mixture is extracted with 200 ml of methylene chloride and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in order. After drying the extract over anhydrous sodium sulfate, the solvent is distilled away under reduced pressure. The resultant residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate:triethylamine=10:10:1 ) to obtain 1.2 g of the desired product as a colorless amorphous.

Workup

  1. additionis dropwise added a solution
  2. customobtained
  3. distillationThe solvent is distilled away under reduced pressure
  4. extractionThe mixture is extracted with 200 ml of methylene chloride
  5. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in order
  6. customAfter drying the
  7. extractionextract over anhydrous sodium sulfate
  8. distillationthe solvent is distilled away under reduced pressure
  9. customThe resultant residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate:triethylamine=10:10:1 )

Sources & evidence

ORD record
ord-e2896bfdb5af492ab592cd33ae9bf1c9
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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