Dicyclohexylcarbodiimide → 1-[4-(Morpholino)butyryloxy]-3-(4-fluorophenyl-1-methylbutyl)-trimethyl-6a,7,8,10a-tetrahydrodibenzo [b,d]pyran hydrobromide

HRID 2398896Notes

Reaction equation

HRID 2398896 reaction equation
[OH:1][C:2]1[C:11]2[CH:10]3[CH:12]=[CH:13][CH2:14][CH2:15][CH:9]3[CH:8]([CH3:16])[O:7][C:6]=2[C:5]([CH3:17])=[C:4]([C:18]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([CH3:22])[CH2:19][CH2:20][CH3:21])[C:3]=1[CH3:30].[BrH:31].[O:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][C:41](O)=[O:42])[CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[BrH:31].[O:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][C:41]([O:1][C:2]2[C:11]3[CH:10]4[CH:12]=[CH:13][CH2:14][CH2:15][CH:9]4[CH:8]([CH3:16])[O:7][C:6]=3[C:5]([CH3:17])=[C:4]([C:18]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)([CH3:22])[CH2:19][CH2:20][CH3:21])[C:3]=2[CH3:30])=[O:42])[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 68121683gamma-Morpholinobutyric acid hydrobromideHCID 681217831-Hydroxy-3-(4-fluorophenyl-1-methylbutyl)-trimethyl-6a,7,8,10a-tetrahydrodibenzo[b,d] pyran

Product 1

HCID 867347831-[4-(Morpholino)butyryloxy]-3-(4-fluorophenyl-1-methylbutyl)-trimethyl-6a,7,8,10a-tetrahydrodibenzo [b,d]pyran hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.54 g. (11.27 mmole) of 1-Hydroxy-3-(4-fluorophenyl-1-methylbutyl)-trimethyl-6a,7,8,10a-tetrahydrodibenzo[b,d] pyran, 2.86 g. (11.27 mmole) of γ-morpholinobutyric acid hydrobromide and 2.50 g. (12.12 mole) of dicyclohexylcarbodiimide are combined in 200 ml. of methylene chloride and stirred at room temperature for 24 hours. The reaction mixture is cooled and the by-product of dicyclohexylurea is removed by filtration. The volume of methylene chloride is removed by filtration. The volume of methylene chloride is reduced and 25 ml. of cyclohexane is added. The mixture is cooled and the small amount of solid which forms is removed by filtration. All solvents are removed on a rotary evaporator and the residue is dried in vacuo. The resulting material is dissolved in a mixture of benzene and ether and placed in cold storage to yield the crystalline product.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe by-product of dicyclohexylurea is removed by filtration
  3. customThe volume of methylene chloride is removed by filtration
  4. additionof cyclohexane is added
  5. temperatureThe mixture is cooled
  6. customthe small amount of solid which forms is removed by filtration
  7. customAll solvents are removed on a rotary evaporator
  8. customthe residue is dried in vacuo
  9. dissolutionThe resulting material is dissolved in a mixture of benzene and ether
  10. customto yield the crystalline product

Sources & evidence

ORD record
ord-e3802c3afa5140548a884e230ee39227
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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