Dicyclohexylcarbodiimide → HCID 68121019, compound

HRID 2398897Notes

Reaction equation

HRID 2398897 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:14]=[C:15]([OH:30])[C:16]3[C:21]4[CH2:22][CH:23]([CH3:26])[CH2:24][CH2:25][C:20]=4[C:19]([CH3:28])([CH3:27])[O:18][C:17]=3[CH:29]=2)([CH3:12])[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[ClH:31].[N:32]1([CH2:38][CH2:39][CH2:40][C:41](O)=[O:42])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:31].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:12])([C:13]2[CH:14]=[C:15]([O:30][C:41](=[O:42])[CH2:40][CH2:39][CH2:38][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[C:16]3[C:21]4[CH2:22][CH:23]([CH3:26])[CH2:24][CH2:25][C:20]=4[C:19]([CH3:28])([CH3:27])[O:18][C:17]=3[CH:29]=2)[CH2:9][CH2:10][CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 131720814-(Piperidin-1-yl)butanoic acid hydrochlorideHCID 54306291HCID 54306291, compound

Product 1

HCID 68121019HCID 68121019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g. (6.76 mmole) of 3-(4-fluorophenyl-1-methylbutyl)-1-hydroxy-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran is combined with 1.41 g. (6.76 mmole) of γ-piperidinobutyric acid hydrochloride and 1.48 g. (7.16 mmole) of dicyclohexylcarbodiimide in 125 ml. of methylene chloride and stirred at room temperature for 16 hours. The by-product of dicyclohexylurea is removed by filtration and the filtrate is evaporated to a residue. The residue is dissolved in ether and the small amount of solid which appears is removed by filtration. The ether is removed on a rotary evaporator and the gummy residue which remains is triturated several times with small quantities of hexane. The material is thoroughly dried to yield the product as a powder.

Workup

  1. customThe by-product of dicyclohexylurea is removed by filtration
  2. customthe filtrate is evaporated to a residue
  3. dissolutionThe residue is dissolved in ether
  4. customthe small amount of solid which appears is removed by filtration
  5. customThe ether is removed on a rotary evaporator
  6. customthe gummy residue which remains is triturated several times with small quantities of hexane
  7. customThe material is thoroughly dried

Sources & evidence

ORD record
ord-3ff761837ab34e268e0a5a02f81793b9
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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