Dicyclohexylcarbodiimide → HCID 21409746, compound

HRID 2071972Notes

Reaction equation

HRID 2071972 reaction equation
[OH:1][C:2]1[C:11]2[C:10]3[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][C:9]=3[C:8]([CH3:18])([CH3:17])[O:7][C:6]=2[CH:5]=[C:4]([CH:19]([CH3:29])[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[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[C:10]4[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][C:9]=4[C:8]([CH3:17])([CH3:18])[O:7][C:6]=3[CH:5]=[C:4]([CH:19]([CH3:29])[CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:3]=2)=[O:41])[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 410866,6,9-Trimethyl-3-(5-phenylpentan-2-yl)-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran-1-olHCID 127337464-Morpholin-4-Yl-Butyric Acid Hydrochloride

Product 1

HCID 21409746HCID 21409746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.91 g. (2.33 mmoles) of 1-hydroxy-3-(4-phenyl-1-methylbutyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-5H-dibenzo [b,d]pyran, prepared according to the method of Example 4, 0.48 g. (2.28 mmoles) of γ-morpholinobutyric acid hydrochloride (Cruickshank 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-f58d0c558e834b4fb6beaef6004fe971
Source dataset
uspto-grants-1977_09
Patent number
US04049653

Reaction notes

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