Water → Phenserine

HRID 2299321Notes

Reaction equation

HRID 2299321 reaction equation
[CH3:1][C@:2]12[C:9]3[CH:10]=[C:11]([OH:14])[CH:12]=[CH:13][C:8]=3[N:7]([CH3:15])[C@H:6]1[N:5]([CH3:16])[CH2:4][CH2:3]2.C([Li])CCC.[C:22]1([N:28]=[C:29]=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C(COC)OC>[CH3:1][C@:2]12[C:9]3[CH:10]=[C:11]([O:14][C:29]([NH:28][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:30])[CH:12]=[CH:13][C:8]=3[N:7]([CH3:15])[C@H:6]1[N:5]([CH3:16])[CH2:4][CH2:3]2

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 119198EserolineHCID 178418339Butyllithium

Product 1

HCID 192706PhenserineYield 96,456.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Eseroline base (50 g, 0.229 mol) was dissolved in 400 mL anhydrous dimethoxyethane under an argon atmosphere. Catalytic amounts of 2.5 M n-butyl lithium in hexanes (6.4 mL, 16 mmol) were added within 1 minute and the solution stirred for 10 minutes. Phenyl isocyanate (27.269 g, 0.2286 mmol) was added over 32 minutes keeping the temperature between 20 and 23° C. The reaction solution was stirred at r.t. for 2 hours 20 minutes, then transferred to an addition funnel. The reaction solution was added over 49 minutes to mixture of DI water (630 mL) and dimethoxyethane (42 mL) under vigorous stirring. The obtained slurry was stirred for 30 minutes, then filtered via a Buchner funnel (Whatman #3 filterpaper). The solid residue was washed four times with DI water (100 mL each) and once with heptane (100 mL), then dried at 45° C. and >29 inches of vacuum for 9 hours. Phenserine base (74.4 g) was obtained as reddish solid in 96.2% yield and 95.1% purity.

Workup

  1. customthe temperature between 20 and 23° C
  2. stirringThe reaction solution was stirred at r.t. for 2 hours 20 minutes
  3. customtransferred to an addition funnel
  4. stirringThe obtained slurry was stirred for 30 minutes
  5. filtrationfiltered via a Buchner funnel (Whatman #3 filterpaper)
  6. washThe solid residue was washed four times with DI water (100 mL each)
  7. dry with materialonce with heptane (100 mL), then dried at 45° C.
  8. wait>29 inches of vacuum for 9 hours

Sources & evidence

ORD record
ord-72e00132dab244c2a805eae1fe56b228
Source dataset
uspto-grants-2002_12
Patent number
US06495700B1

Reaction notes

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