Dichloromethane → HCID 131710799, compound

HRID 2398865Notes

Reaction equation

HRID 2398865 reaction equation
[CH3:1][C:2]1([CH3:31])[C:23]2[CH2:24][CH2:25][N:26]([CH2:28][C:29]#[CH:30])[CH2:27][C:22]=2[C:5]2[C:6]([OH:21])=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[CH:9][C:4]=2[O:3]1.C1(N=[C:39]=[N:40][CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43]C2)CCCCC1.C(Cl)[Cl:48]>>[ClH:48].[CH3:31][C:2]1([CH3:1])[C:23]2[CH2:24][CH2:25][N:26]([CH2:28][C:29]#[CH:30])[CH2:27][C:22]=2[C:5]2[C:6]([O:21][C:2](=[O:3])[CH2:23][CH2:22][CH2:39][N:40]3[CH2:41][CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH:16]([CH3:20])[CH2:17][CH2:18][CH3:19])=[CH:9][C:4]=2[O:3]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 20361130HCID 20361130, compound

Product 1

HCID 131710799HCID 131710799, compound

Procedure

A mixture of 1.45 g. (4.26 mm) of 5,5-dimethyl-10-hydroxy-2-(2-propynyl)-8-(1-methylbutylphenyl)-1,2,3,4-tetrahydro-5H[1]benzopyrano[3,4-d]pyridine, 0.89 g. (4.28 mm.) of Δ-piperidinobutyric acid hydrochloride and 0.93 g. (4.50 mm.) of dicyclohexylcarbodiimide in 200 ml. of methylene chloride are stirred at room temperature for 18 hours. After cooling the reaction mixture for 11/2 hours, the by-product of dicyclohexylurea is removed by suction filtration. A rotary evaporator is used to remove the methylene chloride, and a mixture of 25 ml. of methylene chloride and 50 ml. of cyclohexane is added. After standing at room temperature for 2 hours and a 5° C. for 16 hours, gravity filtration is used to separate the resulting solid. This material is generally a mixture of the starting acid hydrochloride and the hydrochloride salt of the starting benzopyran. The mother liquid is evaporated and the residue crystallized from a mixture of 2 ml. of methylene chloride and 15 ml. of diethyl ether. After filtration and drying, the pure product is obtained.

Workup

  1. additionA mixture of 1.45 g
  2. temperatureAfter cooling the reaction mixture for 11/2 hours
  3. customthe by-product of dicyclohexylurea is removed by suction filtration
  4. customA rotary evaporator
  5. customto remove the methylene chloride
  6. additiona mixture of 25 ml
  7. additionof cyclohexane is added
  8. filtrationgravity filtration
  9. customto separate the resulting solid
  10. additiona mixture of the starting acid hydrochloride
  11. customThe mother liquid is evaporated
  12. customthe residue crystallized from a mixture of 2 ml
  13. filtrationAfter filtration
  14. customdrying
  15. customthe pure product is obtained

Sources & evidence

ORD record
ord-16260609f6934641b8d73514dbfeab15
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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