Triethylamine → 5,5-Dimethyl-10-[3-(piperidino)propionyloxy]-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano [3,4-d]pyridine dihydrochloride

HRID 441889Notes

Reaction equation

HRID 441889 reaction equation
CC1(C)[C:21]2[CH2:22][CH2:23][N:24](CC#C)[CH2:25][C:20]=2C2C(O)=CC(C(C(C)CCCCC)C)=CC=2O1.C(N(CC)CC)C.C([Cl:41])(=O)C=C.[C:42]([O:46][C:47]1[C:52]2[C:53]3[CH2:58][N:57]([CH2:59][C:60]#[CH:61])[CH2:56][CH2:55][C:54]=3[C:62]([CH3:65])([CH3:64])[O:63][C:51]=2[CH:50]=[C:49]([CH:66]([CH:68]([CH3:74])[CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH3:67])[CH:48]=1)(=[O:45])[CH:43]=[CH2:44]>CO.C(Cl)(Cl)Cl.C(Cl)Cl>[ClH:41].[ClH:41].[CH3:65][C:62]1([CH3:64])[C:54]2[CH2:55][CH2:56][N:57]([CH2:59][C:60]#[CH:61])[CH2:58][C:53]=2[C:52]2[C:47]([O:46][C:42](=[O:45])[CH2:43][CH2:44][N:24]3[CH2:25][CH2:20][CH2:21][CH2:22][CH2:23]3)=[CH:48][C:49]([CH:66]([CH:68]([CH3:74])[CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])[CH3:67])=[CH:50][C:51]=2[O:63]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 990408-(1,2-Dimethylheptyl)-1,3,4,5-tetrahydro-5,5-dimethyl-2-(2-propyn-1-yl)-2H-(1)benzopyrano(4,3-c)pyridin-10-olHCID 2141812210-acryloyloxy-5,5-dimethyl-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine

Product 1

HCID 214181205,5-Dimethyl-10-[3-(piperidino)propionyloxy]-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano [3,4-d]pyridine dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of 2.0 g. (5.05 mmole) of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-d]pyridine, 0.75 ml. (5.30 mmole) of triethylamine, 0.42 ml. (5.30 mmole) of acryloyl chloride and 25 ml. of methylene chloride was stirred at room temperature for 18 hours. The reaction mixture was evaporated and 50 ml. of diethyl ether was added to the brown semi-solid residue which was obtained. The insoluble solid was removed by filtration, and the mother liquor was removed on a rotary evaporator. The residue which remained was subsequently dissolved in 50 ml. of methylene chloride. After washing twice with 1N hydrochloric acid, twice with 5% sodium bicarbonate solution, twice with water, and drying over sodium sulfate, the methylene chloride was evaporated to give 1.86 g. (82%) of 10-acryloyloxy-5,5-dimethyl-8-(3-methyl-2-octyl)-2-(2-propynyl)-1,2,3,4-tetrahydro-5H-[1]benzopyrano[ 3,4-d]pyridine as a brown gum. The material showed a single spot by thin layer chromatography (5% MeOH/CHCl3), and the infrared and nuclear magnetic resonance spectra were consistent with the desired product.

Workup

  1. additionA mixture of 2.0 g
  2. customThe reaction mixture was evaporated
  3. additionof diethyl ether was added to the brown semi-solid residue which
  4. customwas obtained
  5. customThe insoluble solid was removed by filtration
  6. customthe mother liquor was removed on a rotary evaporator
  7. dissolutionThe residue which remained was subsequently dissolved in 50 ml
  8. washAfter washing twice with 1N hydrochloric acid, twice with 5% sodium bicarbonate solution, twice with water
  9. dry with materialdrying over sodium sulfate
  10. customthe methylene chloride was evaporated
  11. customto give 1.86 g

Sources & evidence

ORD record
ord-82536c5d9b394ef28fc4ae65198ee6df
Source dataset
uspto-grants-1977_08
Patent number
US04042694

Reaction notes

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