Butylamine → HCID 59289846, compound

HRID 1496839Notes

Reaction equation

HRID 1496839 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]23[O:16][C:15](=[O:17])[CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10]3)=[O:8])=[CH:5][CH:4]=1.[CH2:20]([NH2:24])[CH2:21][CH2:22][CH3:23]>COC(C)(C)C>[CH2:20]([NH:24][C:15]([CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1([C:7](=[O:8])[C:6]1[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[OH:16])=[O:17])[CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 86629708HCID 86629708, compound

Product 1

HCID 59289846HCID 59289846, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

20.8 g (0.08 mol) of 6-(4-methoxy-benzoyl)-7-oxa-bicyclo[4.2.0]octan-8-one (example 10) are dissolved in 200 ml of tert-butyl methyl ether. 10.46 g (0.143 mol) of n-butylamine are slowly added to this solution over one hour. The reaction mixture is stirred overnight at room temperature and the solvent is subsequently distilled off under vacuum. The yellowish oil thus obtained crystallizes upon standing and is purified by recrystallization from heptane. 22.5 g (85%) 2-(4-methoxybenzoyl)-2-hydroxy-cyclohexanecarboxylic acid butyl-amide are thus obtained as white solid with a melting point of 94-95° C.

Workup

  1. distillationthe solvent is subsequently distilled off under vacuum
  2. customThe yellowish oil thus obtained
  3. customcrystallizes
  4. customis purified by recrystallization from heptane

Sources & evidence

ORD record
ord-c56a18971b7f4989833156ac2f21a603
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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