Maleic Acid → (+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleate

HRID 1363684Notes

Reaction equation

HRID 1363684 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH3:3].[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]\[C:21]([OH:23])=[O:22]>C(OCC)(=O)C>[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]\[C:21]([OH:23])=[O:22].[CH3:3][N:2]([CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)[CH3:1]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 9813414Faxeladol

Product 1

HCID 16042847(+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleateYield 97.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

2.33 g of (+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol are dissolved at room temperature in 15 ml of ethyl acetate and 1.16 g of maleic acid are dissolved in 30 ml of ethyl acetate, each in a glass flask. In another glass flask, 20 ml of ethyl acetate are heated to 45° C. and then both solutions are added simultaneously dropwise with stirring. Considerable turbidity forms spontaneously. Once addition is complete, the suspension is stirred for another 3 hours at 50° C. Then it is left to cool by itself to room temperature. The precipitate is filtered out and washed once with 10 ml of ethyl acetate and dried by having air drawn through it (5 minutes). 3.41 g (97.7% of theoretical) of (+)-(1R,2R)-3-[2-(dimethylamino)methyl-(cyclohex-1-yl)]-phenol maleate are obtained as crystalline form A (according to the X-ray diffraction pattern). DSC analysis reveals two peaks at 166.03 and 177.03° C.

Workup

  1. additionboth solutions are added simultaneously dropwise
  2. additionOnce addition
  3. stirringthe suspension is stirred for another 3 hours at 50° C
  4. waitThen it is left
  5. filtrationThe precipitate is filtered out
  6. washwashed once with 10 ml of ethyl acetate
  7. customdried
  8. customdrawn through it (5 minutes)

Sources & evidence

ORD record
ord-ed0d21b1a7f841d3ad3807647efc57d1
Source dataset
uspto-grants-2011_02
Patent number
US07884247B2

Reaction notes

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