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Hydrochloric Acid → HCID 54527635, compound

HRID 1701105
Notes
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Reaction equation

HRID 1701105 reaction equation
[CH2:1]([C:3]1([CH3:22])[CH:8]([CH3:9])[CH:7]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][C:5]([CH2:20][CH3:21])([CH3:19])[NH:4]1)[CH3:2].Cl.[CH2:24]1[O:26][CH2:25]1>CO>[OH:26][CH2:25][CH2:24][N:4]1[C:5]([CH2:20][CH3:21])([CH3:19])[CH2:6][CH:7]([NH:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]([CH3:9])[C:3]1([CH2:1][CH3:2])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 22486017N-(2,6-Diethyl-2,3,6-trimethylpiperidin-4-yl)benzamide

Product 1

HCID 54527635HCID 54527635, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

30.3 g of 2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine (compound no. 9), 200 ml of methanol and 2 ml of concentrated hydrochloric acid are introduced into an autoclave. About 9 g of ethyleneoxide are added, and the contents of the autoclave are heated to 130° C. for 30 hours. After cooling, the contents of the autoclave are purified by filtration, and the methanol is evaporated. Crystallization of the residue from toluene yields 1-β-hydroxyethyl-2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine (compound no. 27); m.p. 212°-214° C. If, instead of 30.3 g of 2,6-diethyl-2,3,6-trimethyl-4-benzamidopiperidine an equimolar amount of N,N'-diacetyl-N,N'-bis-(2,6-diethyl-2,3,6-trimethyl-4-piperidyl)-hexamethylene-1,6-diamine (compound no. 22), 12 g instead of 9 g of ethyleneoxide are used and otherwise the procedure described above is followed, N,N'-diacetyl-N,N'-bis-(1-β-hydroxyethyl-2,6-diethyl-2,3,6-trimethyl-4-piperidyl)-hexamethylene-1,6-diamine (compound no. 28) is obtained as a yellowish viscous resin.

Workup

  1. temperatureAfter cooling
  2. filtrationthe contents of the autoclave are purified by filtration
  3. customthe methanol is evaporated
  4. customCrystallization of the residue from toluene

Sources & evidence

ORD record
ord-616ba2544c5b4ec98879ce4fb1f4a6ec
Source dataset
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04191683

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes