(3-Bromopropyl)benzene → HCID 131715160, compound

HRID 979536Notes

Reaction equation

HRID 979536 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][C@@:6]12[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[C:9]1[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=1[O:7]2.Br[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+].[C:34]([O-:39])(=[O:38])[C:35]([O-:37])=[O:36]>CN(C=O)C.CCOCC>[OH2:7].[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[C:23]1([CH2:22][CH2:21][CH2:20][N:3]([CH2:4][CH2:5][C@@:6]23[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[O:7]3)[CH3:2])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:23]1([CH2:22][CH2:21][CH2:20][N:3]([CH2:4][CH2:5][C@@:6]23[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]=2[O:7]3)[CH3:2])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36]

Participants

7

Reactant 4

HCID 12503(3-Bromopropyl)benzeneHCID 71081OxalateHCID 516892Sodium BicarbonateHCID 70349536HCID 70349536, compound

Product 1

HCID 131715160HCID 131715160, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
87 °C

Procedure

To a mixture of 4.08 g (0.018 m) of cis-1,2,3,4,4a,9b-hexahydro-4a-(2-methylaminoethyl)dibenzofuran of Example 11 and 4.38 g (0.022 m) of 1-bromo-3-phenylpropane in 60 ml DMF, 3.8 g (0.045 m) of NaHCO3 was added under nitrogen. The reaction mixture was warmed to 87° C. and held there overnight (about 16 hours). The temperature was raised to 108° C. for 4 hours, the NaHCO3 filtered off and the mixture partitioned between water and ethyl acetate. The ethylacetate layer was dried over Na2SO4 and evaporated to give an oil. The resultant oil was converted to an oxalate in ether as in Example 4 and recrystallized from ethyl acetate to give 2.2 g (28%) of cis-1,2,3,4,4a,9b-hexahydro-4a-[2-[-N-(3-phenylpropyl)-N-methylamino]ethyl]dibenzofuran oxalate hemihydrate m.p. 104°-105° C.

Workup

  1. additionwas added under nitrogen
  2. custom(about 16 hours)
  3. temperatureThe temperature was raised to 108° C. for 4 hours
  4. filtrationthe NaHCO3 filtered off
  5. customthe mixture partitioned between water and ethyl acetate
  6. dry with materialThe ethylacetate layer was dried over Na2SO4
  7. customevaporated
  8. customto give an oil
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a0e70957775e44b388f8bdb6caf9ecdb
Source dataset
uspto-grants-1987_05
Patent number
US04668690

Reaction notes

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