Promethazine → promethazine dibenzoyl-D-tartrate

HRID 473791

Reaction equation

HRID 473791 reaction equation
[CH3:1][CH:2]([N:18]([CH3:20])[CH3:19])[CH2:3][N:4]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2.C([C@H]([C@@H](C([O-])=O)O)O)([O-])=O.CC(N(C)C)CN1C2C=CC=CC=2SC2C=CC=CC1=2.[C:51]([C@:59]([C:74]([OH:76])=[O:75])([OH:73])[C@:60]([C:65](=[O:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)([OH:64])[C:61]([OH:63])=[O:62])(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CC(C)=O>[CH3:1][CH:2]([N:18]([CH3:19])[CH3:20])[CH2:3][N:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.[C:65]([C@:60]([C:61]([O-:63])=[O:62])([OH:64])[C@:59]([C:51](=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([OH:73])[C:74]([O-:76])=[O:75])(=[O:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

5

Reactant 3

HCID 4927PromethazineHCID 12362977Di-benzoyl-d-tartaric acidHCID 86609044promethazine D-tartrate

Product 1

HCID 131731159promethazine dibenzoyl-D-tartrate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To prepare promethazine-D-tartrate, promethazine (10 g, 0.035 mol) dissolved in 80 ml acetone was heated in a 60° C. bath while dibenzoyl-D-tartaric acid (12.789 g, 0.036 mol) was added. The resulting clear yellow solution was left at ambient temperature for 3 days (step 2). A heavy precipitate formed, which was filtered off and recrystalized from ethanol four times to give 4.0 g promethazine dibenzoyl-D-tartrate white crystals (step 3).

Workup

  1. additionwas added
  2. customA heavy precipitate formed
  3. filtrationwhich was filtered off
  4. customrecrystalized from ethanol four times

Sources & evidence

ORD record
ord-f0c06199abd84d49a9fcb7be2f20aa78
Source dataset
uspto-grants-2014_01
Patent number
US08637503B2

Linked notes

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