4-Methoxybenzoyl isocyanate → HCID 12608517, compound

HRID 225147Notes

Reaction equation

HRID 225147 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH:11]2[O:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][CH2:12]2)[OH:10])[CH2:4][CH2:3]1.[CH3:21][O:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([N:29]=[C:30]=[O:31])=[O:28])=[CH:25][CH:24]=1>[Na].C1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([NH:29][C:30]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([CH:11]3[O:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[O:13][CH2:12]3)[OH:10])[CH2:4][CH2:3]2)=[O:31])=[O:28])=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 125510974-Methoxybenzoyl isocyanateHCID 12608506HCID 12608506, compound

Product 1

HCID 12608517HCID 12608517, compoundYield 15.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 5360545SodiumSolvent

Procedure

Erythro 4-amino-1-[2-(1,4-benzodioxan-2-yl)-2-hydroxy-ethyl]piperidine (2.0 g 0.0072 m)) was dissolved in sodium dried benzene (100 mls). To the stirring solution was added p-methoxy benzoyl isocyanate (1.27 g 0.0072m) in benzene (20 mls) and the solution stirred at room temperature for 18 hours. The solvent was evaporated and the residue heated with isopropyl alcohol. The insoluble solid was filtered off and triturated with hot ethanol, filtered and dried to give the title compound (0.5 g 15%).

Workup

  1. customThe solvent was evaporated
  2. temperaturethe residue heated with isopropyl alcohol
  3. filtrationThe insoluble solid was filtered off
  4. customtriturated with hot ethanol
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-4b00aa69b63848c389bf83606c3625e5
Source dataset
uspto-grants-1980_11
Patent number
US04235915

Reaction notes

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