Succinic Acid → HCID 86620199, compound

HRID 639864Notes

Reaction equation

HRID 639864 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:15][C@@:14]2([CH2:16][O:17][CH3:18])[CH2:13][NH:12][CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:19]([OH:26])(=[O:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23]>C(O)(C)C>[C:19]([OH:26])(=[O:25])[CH2:20][CH2:21][C:22]([OH:24])=[O:23].[Cl:1][C:2]1[CH:3]=[C:4]([C@:9]23[CH2:15][C@@:14]2([CH2:16][O:17][CH3:18])[CH2:13][NH:12][CH2:11][CH2:10]3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 24802841(1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo(4.1.0)heptane

Product 1

HCID 86620199HCID 86620199, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To 300.7 mg of (1S,6R)-6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptane (E2a) and 123.4 mg of succinic acid, 0.5 mL of isopropylalcohol (IPA) was added with stirring. A further 0.5 mL was added and heat applied using an air gun to aid dissolution. Further solvent additions of 2×0.5 mL, 1 mL, 0.5 mL and 1 mL were added to achieve a mobile slurry (giving a total solvent volume of 4.5 mL IPA added). The resulting slurry was temperature cycled between 0 and 40° C. for three days. The sample was then filtered and the solid title compound obtained dried under vacuum at 70° C. for 24 hours.

Workup

  1. additionA further 0.5 mL was added
  2. temperatureheat
  3. dissolutiondissolution
  4. additionFurther solvent additions of 2×0.5 mL, 1 mL, 0.5 mL and 1 mL were added
  5. additionadded)
  6. customtemperature cycled between 0 and 40° C.
  7. customfor three days
  8. filtrationThe sample was then filtered

Sources & evidence

ORD record
ord-14ba9c46766f4cf3838ea84859525e13
Source dataset
uspto-grants-2010_04
Patent number
US07691893B2

Reaction notes

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