Ammonia → HCID 178447560, compound

HRID 614837Notes

Reaction equation

HRID 614837 reaction equation
Cl.OC(CN1CCC(COC2C=CC=CC=2)CC1)COC1C2N=NNC=2C=CC=1.C(OC(=O)C(C)(C)C)(=O)C(C)(C)C.C(O)(=O)C(C)(C)C.N.Cl.Cl.[C:53]([O:59][CH:60]([CH2:72][N:73]1[CH2:78][CH2:77][CH:76]([CH2:79][O:80][C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[CH2:75][CH2:74]1)[CH2:61][O:62][C:63]1[C:71]2[N:70]=[N:69][NH:68][C:67]=2[CH:66]=[CH:65][CH:64]=1)(=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55]>CO>[C:53]([O:59][CH:60]([CH2:72][N:73]1[CH2:74][CH2:75][CH:76]([CH2:79][O:80][C:81]2[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=2)[CH2:77][CH2:78]1)[CH2:61][O:62][C:63]1[C:71]2[N:70]=[N:69][NH:68][C:67]=2[CH:66]=[CH:65][CH:64]=1)(=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55]

Participants

8

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6417Pivalic acidHCID 15234Pivalic anhydrideHCID 178447561HCID 178447561, compoundHCID 178479701HCID 178479701, compound

Product 1

HCID 178447560HCID 178447560, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5.1 g. 4-[2-hydroxy-3-(4-phenoxymethylpiperidino)-propoxy]-benzotriazole hydrochloride, 6.7 g. pivalic anhydride and 33.3 g. molten pivalic acid is stirred for 3 days at ambient temperature, then poured on to ice, neutralized with an aqueous solution of ammonia and extracted with methylene chloride. After evaporation of the extract, the oily residue obtained is taken up in methanol and rendered weakly acidic with dilute hydrochloric acid. Upon evaporating the solvent, there are obtained 2.53 g. (38% of theory) 4-[2-pivaloyloxy-3-(4-phenoxymethylpiperidino)-propoxy]-benzotriazole hydrochloride; m.p. 131°-133° C.

Workup

  1. additionA mixture of 5.1 g
  2. additionpoured on to ice
  3. extractionextracted with methylene chloride
  4. customAfter evaporation of the extract
  5. customthe oily residue obtained
  6. customUpon evaporating the solvent, there
  7. customare obtained 2.53 g

Sources & evidence

ORD record
ord-8693d2e9261d49fb9c28452d0bf6d705
Source dataset
uspto-grants-1979_03
Patent number
US04146630

Reaction notes

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