Acetic Anhydride → 4-benzyloxy-3-acetylamino-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl] benzyl alcohol

HRID 1731094Notes

Reaction equation

HRID 1731094 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([CH:33]=[CH:34][C:35]=1[O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH:12]([OH:32])[CH2:13][N:14]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:15]([CH3:24])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>>[CH2:37]([O:36][C:35]1[CH:34]=[CH:33][C:11]([CH:12]([OH:32])[CH2:13][N:14]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:15]([CH3:24])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)=[CH:10][C:9]=1[NH:8][C:1](=[O:3])[CH3:2])[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 539014743-amino-4-benzyloxy-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)-aminomethyl]benzyl alcohol

Product 1

HCID 681358224-benzyloxy-3-acetylamino-alpha-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl] benzyl alcohol

Procedure

In 20 ml. of acetic anhydride there was dissolved 4.0 g. of 3-amino-4-benzyloxy-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl] benzyl alcohol [A] prepared above and after heating the mixture to 65°-80° C for one hour and 30 minutes, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in a mixture of 15 ml. of methanol and 2.0 g. of potassium hydroxide and the solution was stirred for one hour at room temperature. Then, methanol was distilled off under reduced pressure and after water was added to the residue, the residue was extracted with benzene. The extract was washed with water, dried over anhydrous magnesium sulfate, and dried. Thereafter, by distilling off the solvent, 3.8 g. of a crystalline powder of 4-benzyloxy-3-acetylamino-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl] benzyl alcohol [A] was obtained. By recrystallizing 2.0 g. of the product thus obtained from 20 ml. of ethanol 1.6 g. of the crystalline pure product was obtained, melting at 141°-143° C.______________________________________Elemental analysis for C32H36N2O4 : C(%) H(%) N(%)______________________________________Calculated: 75.55 6.92 5.34Found: 75.62 7.03 5.21______________________________________

Workup

  1. temperatureafter heating the mixture to 65°-80° C for one hour
  2. concentration30 minutes, the reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of 15 ml
  4. distillationThen, methanol was distilled off under reduced pressure
  5. additionafter water was added to the residue
  6. extractionthe residue was extracted with benzene
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customdried
  10. distillationThereafter, by distilling off the solvent, 3.8 g

Sources & evidence

ORD record
ord-a5c4ad90648442e999039b4b247903ea
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Reaction notes

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