Hydrochloric Acid → HCID 54324197, compound

HRID 1940195Notes

Reaction equation

HRID 1940195 reaction equation
[CH:1](N)([CH3:3])[CH3:2].[CH2:5]([Li])CCC.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[NH:20][C:19](=[O:21])[CH2:18][CH2:17][CH:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:15]=2[CH:29]=1.[CH2:30]([O:32][C:33](=[O:36])[CH2:34]I)[CH3:31].Cl>O1CCCC1.CCCCCC>[CH2:30]([O:32][C:33](=[O:36])[CH2:34][CH:18]1[CH2:17][CH:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[C:15]2[CH:29]=[C:11]([Cl:10])[CH:12]=[CH:13][C:14]=2[N:20]([CH2:2][CH:1]([CH3:3])[CH3:5])[C:19]1=[O:21])[CH3:31]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 12183Ethyl iodoacetateHCID 21465910HCID 21465910, compoundHCID 178418339Butyllithium

Product 1

HCID 54324197HCID 54324197, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-15 °C

Procedure

To dry tetrahydrofuran (5 ml) was added isopropylamine (0.25 ml), and the mixture was cooled to -15° C. to which was added a 1.58M hexane solution of n-butyl lithium (1.14 ml), and the mixture was stirred for 45 minutes at -15° C. To the reaction mixture was added 7-chloro-5-(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (0.5 g) dissolved in tetrahydrofuran (5 ml), which was stirred for 15 minutes at 0° C. The reaction mixture was cooled to -78° C., to which was added iodoacetic acid ethyl ester (0.25 ml). The mixture was stirred for 15 minutes at -78° C., then for one hour at 0° C. To the reaction mixture was added 1N hydrochloric acid (50 ml), which was extracted with acetic acid ethyl ester. The acetic acid ethyl ester layer was washed with a saturated aqueous solution of hydrogencarbonate, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by means of a silica-gel column chromatography to give 0.1 g of an oily compound.

Workup

  1. stirringwhich was stirred for 15 minutes at 0° C
  2. temperatureThe reaction mixture was cooled to -78° C., to which
  3. stirringThe mixture was stirred for 15 minutes at -78° C.
  4. waitfor one hour at 0° C
  5. extractionwas extracted with acetic acid ethyl ester
  6. washThe acetic acid ethyl ester layer was washed with a saturated aqueous solution of hydrogencarbonate
  7. dry with materialby drying over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by means of a silica-gel column chromatography

Sources & evidence

ORD record
ord-97d38c7b57b8465789a3c09519ad4327
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

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