Hydrochloric Acid → HCID 68828005, compound

HRID 1786511Notes

Reaction equation

HRID 1786511 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]2[CH2:15][CH2:14][C:13]([N:22]([CH3:24])[CH3:23])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[ClH:25]>CC(=O)CC>[ClH:25].[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH:10]2[CH2:15][CH2:14][C:13]([N:22]([CH3:24])[CH3:23])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1.[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH:10]2[CH2:15][CH2:14][C:13]([N:22]([CH3:24])[CH3:23])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68828005HCID 68828005, compound

Product 2

HCID 68828005HCID 68828005, compoundHCID 68831952HCID 68831952, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

As described for Example 5, 69 mg of the second most polar diastereoisomer of {4-[2-(4-fluorophenyl)vinyl]-1-phenylcyclohexyl}dimethylamine were also obtained (yellow oil) which were dissolved in 2-butanone (1.5 ml), and subsequently 3.3M ethanolic HCl (194 μl, 0.6 mmole) was added and the mixture stirred for 2 h. After evaporating to dryness the residue was dissolved in two drops of MeOH, and subsequently ether (8 ml) was added. The resultant residue was suction filtered and washed with ether (2×1 ml). The hydrochloride of the second most polar diastereoisomer of {4-[2-(4-fluorophenyl)vinyl]-1-phenylcyclohexyl)dimethylamine was thus obtained as a white solid (70 mg, mp 177 to 188° C.).

Workup

  1. customwere also obtained (yellow oil) which
  2. customAfter evaporating to dryness the residue
  3. dissolutionwas dissolved in two drops of MeOH
  4. additionsubsequently ether (8 ml) was added
  5. filtrationfiltered
  6. washwashed with ether (2×1 ml)

Sources & evidence

ORD record
ord-b9baa8b938bb4678b620f56fdeca6529
Source dataset
uspto-grants-2009_03
Patent number
US07507758B2

Reaction notes

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