Dicyclohexylcarbodiimide → HCID 21406093, compound

HRID 972174Notes

Reaction equation

HRID 972174 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](O)=[O:9])([CH3:4])([CH3:3])[CH3:2].[NH2:19][CH:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23][C:22]([CH3:29])([CH3:28])[CH2:21]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:28][C:22]1([CH3:29])[CH2:21][CH:20]([NH:19][C:8](=[O:9])[C:7]2[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:13]([OH:14])=[C:12]([C:15]([CH3:17])([CH3:16])[CH3:18])[CH:11]=2)[CH2:25][C:24]([CH3:27])([CH3:26])[NH:23]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 375244-Amino-2,2,6,6-tetramethylpiperidine

Product 1

HCID 21406093HCID 21406093, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 25 grams (0.1 mole) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 15.6 grams (0.1 mole) of 4-amino-2,2,6,6-tetramethylpiperidine in 100 milliliters of dry tetrahydrofuran was added dropwise a solution of 20.6 grams (0.1 mole) of dicyclohexylcarbodiimide in 75 milliliters of dry tetrahydrofuran. The mixture was stirred for several hours and the white solid (dicyclohexyl urea) was filtered off and discarded. Evaporation of the filtrate gave a white solid, which was recrystallized from 1:1 benzenehexane to give N-(2,2,6,6-tetramethyl-4-piperidinyl)-3,5-di-t-butyl-4-hydroxybenzamide; melting point 256°-258° C.

Workup

  1. filtrationthe white solid (dicyclohexyl urea) was filtered off
  2. customEvaporation of the filtrate
  3. customgave a white solid, which
  4. customwas recrystallized from 1:1 benzenehexane

Sources & evidence

ORD record
ord-d59ad37517a747c4b1340b6ef6df8f51
Source dataset
uspto-grants-1977_10
Patent number
US04052361

Reaction notes

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