Methanol → N2-Acetyl-L-glutamine

HRID 1857024Notes

Reaction equation

HRID 1857024 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([NH2:18])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([NH:22][C@H:23]([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][C:26](=[O:28])[NH2:27])(=[O:21])[CH3:20].CO>CC(C)=O>[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C@@H:13]([NH2:18])[CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([NH:22][C@H:23]([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][C:26](=[O:28])[NH2:27])(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 887MethanolHCID 182230N2-Acetyl-L-glutamineHCID 104220523-Methyl-1-(2-piperidino-phenyl)-1-butylamine

Product 2

HCID 182230N2-Acetyl-L-glutamineHCID 105146093-Methyl-1-(2-piperidinophenyl)-1-butylamine, (S)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 122 g (0.495 mol) of racemic 1-(2-piperidino-phenyl)-3-methyl-1-butylamine in 1000 ml of acetone is mixed with 93.7 g (0.495 mol) of N-acetyl-L-glutaminic acid. The mixture is refluxed over a vapour bath and methanol is added in batches (a total of about 80 ml) until a clear solution is obtained. After this has been left to cool and stand overnight at ambient temperature, the crystals obtained are removed by suction filtering, washed twice with 200 ml of cold acetone at -15° C. and then dried. The product obtained [98.9 g; melting point: 163-166° C.; [α]D20 =+0.286° (c=1 in methanol)] is recrystallised from 1000 ml of acetone with the addition of 200 ml of methanol, thereby obtaining the (S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine as the addition salt of N-acetyl-L-glutaminic acid.

Workup

  1. temperatureThe mixture is refluxed over a vapour bath
  2. customis obtained
  3. waitAfter this has been left
  4. temperatureto cool
  5. customthe crystals obtained
  6. customare removed by suction
  7. filtrationfiltering
  8. washwashed twice with 200 ml of cold acetone at -15° C.
  9. customdried
  10. customThe product obtained [98.9 g; melting point: 163-166° C.; [α]D20 =+0.286° (c=1 in methanol)]
  11. customis recrystallised from 1000 ml of acetone with the addition of 200 ml of methanol

Sources & evidence

ORD record
ord-95f3239a1a7046e58e6286d9fd88c2ef
Source dataset
uspto-grants-2000_11
Patent number
US06143769

Reaction notes

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