Dicyclohexylcarbodiimide → HCID 21433911, compound

HRID 2398891Notes

Reaction equation

HRID 2398891 reaction equation
[OH:1][C:2]1[C:11]2[CH:10]3[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH3:23])[CH2:20][CH2:21][CH3:22])[CH:3]=1.[ClH:30].[O:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][C:40](O)=[O:41])[CH2:33][CH2:32]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:30].[O:31]1[CH2:36][CH2:35][N:34]([CH2:37][CH2:38][CH2:39][C:40]([O:1][C:2]2[C:11]3[CH:10]4[CH:12]=[C:13]([CH3:16])[CH2:14][CH2:15][CH:9]4[C:8]([CH3:18])([CH3:17])[O:7][C:6]=3[CH:5]=[C:4]([C:19]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([CH3:23])[CH2:20][CH2:21][CH3:22])[CH:3]=2)=[O:41])[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 127337464-Morpholin-4-Yl-Butyric Acid HydrochlorideHCID 86734782HCID 86734782, compound

Product 1

HCID 21433911HCID 21433911, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.7 g. (2.33 mmoles) of 1-Hydroxy-3-(phenyl- 1-methylbutyl)-6,6,9-trimethyl-6a,7,8,10a-tetrahydrodibenzo [b,d]pyran, prepared according to the method of Example 48, 0.48 g. (2.28 mmoles) of γ-morpholinobutyric acid hydrochloride (Cruichshank and Sheehan, J. Am. Chem. Soc. 83, 2891 (1961), m.p. 180°-182° ) and 0.48 g. (2.35 mmoles) of dicyclohexylcarbodiimide (Aldrich) are combined with 35 ml. of methylene chloride and stirred at room temperature for a total of 40 hours. The insoluble by-product of dicyclohexylurea is removed using a rotary evaporator. The resulting residue is dissolved in about 20 ml. of benzene and a small amount of insoluble material is removed by filtration. The benzene is evaporated and the residue dried in vacuo to give 0.7 g. of material. Crystallization from benzene/pet ether yields the crystalline product.

Workup

  1. customThe insoluble by-product of dicyclohexylurea is removed
  2. customa rotary evaporator
  3. dissolutionThe resulting residue is dissolved in about 20 ml
  4. customof benzene and a small amount of insoluble material is removed by filtration
  5. customThe benzene is evaporated
  6. customthe residue dried in vacuo
  7. customto give 0.7 g
  8. customCrystallization from benzene/pet ether
  9. customyields the crystalline product

Sources & evidence

ORD record
ord-2990dcb64e3241529111c16fb15146a8
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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