Benzene → HCID 67904803, compound

HRID 362202Notes

Reaction equation

HRID 362202 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].C([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C.[N:20]1([C:26](Cl)=[O:27])CCCCC1.[CH:29]1C=CC=CC=1>>[N:15]1([NH:20][C:26]([O:12][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4][N:2]([CH3:1])[CH3:3])=[O:27])[CH2:16][CH2:17][CH2:29][CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Product 1

HCID 67904803HCID 67904803, compound

Procedure

A mixture prepared from 4-[[(dimethylamino)methylene]amino]-3-pyridinol (5.2 g), triethylamine (4.8 mL), piperidine carbonyl chloride (4.89 mL) and benzene (173 mL) was refluxed for a half hour, cooled, poured directly onto a silica column and eluted with 5% Et3N/ethyl acetate to yield 7.55 g of product. Recrystallization from ethyl acetate and drying under high vacuum for 2 hours yielded 5.5 g of crystals, m.p. 90°-91 ° C.

Workup

  1. temperaturewas refluxed for a half hour
  2. temperaturecooled
  3. additionpoured directly onto a silica column
  4. washeluted with 5% Et3N/ethyl acetate

Sources & evidence

ORD record
ord-1d30db78e69545e2932c2dca2e51f457
Source dataset
uspto-grants-1999_02
Patent number
US05869480

Reaction notes

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