Triethylamine → HCID 13189010, compound

HRID 1995287Notes

Reaction equation

HRID 1995287 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:5]=2[CH:4]=1.[ClH:18].[Cl:19][CH2:20][CH2:21][N:22]1[CH2:28][CH:27]2[CH2:29][CH2:30][CH:24]([CH2:25][CH2:26]2)[CH2:23]1.C(N(CC)CC)C>C(O)C>[ClH:19].[ClH:18].[CH:27]12[CH2:29][CH2:30][CH:24]([CH2:25][CH2:26]1)[CH2:23][N:22]([CH2:21][CH2:20][N:12]1[CH2:13][CH2:14][C:9]3[C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[O:16][C:15](=[O:17])[C:10]=3[CH2:11]1)[CH2:28]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

HCID 13189010HCID 13189010, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-methoxy-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (2.31 g, 0.01 mole), 3-(2-chloroethyl)-3-azabicyclo(3.2.2)nonane hydrochloride (2.49 g, 0.01 mole) and triethylamine (3.03 g) in absolute ethanol (50 ml) is refluxed for 24 hours. The reaction mixture is filtered. Hydrogen chloride gas is bubbled through the filtrate. The product is filtered off, washed with ethanol and sucked dry. Recrystallization from methanol gave the product (2.34 g), mp 265°-270° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationThe reaction mixture is filtered
  3. customHydrogen chloride gas is bubbled through the filtrate
  4. filtrationThe product is filtered off
  5. washwashed with ethanol
  6. customsucked dry
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-214677168f554228a8edc1147628bd49
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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