Triethylamine → HCID 131713583, compound

HRID 1462460Notes

Reaction equation

HRID 1462460 reaction equation
[CH3:1][NH:2][C@H:3]1[C@H:12]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:11][CH2:10][CH2:9][C:4]21[O:8][CH2:7][CH2:6][O:5]2.C(N(CC)CC)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH2:33][C:34](Cl)=[O:35])[CH:29]=[CH:30][C:31]=1[Cl:32]>C(OCC)C>[ClH:25].[Cl:25][C:26]1[CH:27]=[C:28]([CH2:33][C:34]([N:2]([CH3:1])[C@H:3]2[C@H:12]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:11][CH2:10][CH2:9][C:4]32[O:5][CH2:6][CH2:7][O:8]3)=[O:35])[CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27581492-(3,4-Dichlorophenyl)acetyl chlorideHCID 86739537HCID 86739537, compound

Product 1

HCID 131713583HCID 131713583, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 0.03 mole of trans-(±)-1-[6-methylamino-1,4-dioxaspiro[4.5]dec-7-yl]pyrrolidine in 200 ml of diethyl ether and 0.036 mole of triethylamine, there is added a solution of 0.036 mole of 3,4-dichlorophenylacetyl chloride in 300 ml of diethyl ether over 30 minutes under nitrogen. After two hours the mixture is filtered and the solid washed with diethyl ether. The combined ethereal layers were washed with water, 10% sodium hydroxide in water solution, water, brine, dried over magnesium sulfate and concentrated in vacuo. The residue is treated with a diethyl ether solution of hydrogen chloride and the resultant precipitate is recrystallized from a methanol/ethyl acetate mixture to give trans-(±)-3,4-dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1,4-dioxaspiro[4.5]-dec-6-y]benzeneacetamide, monohydrochloride.

Workup

  1. filtrationAfter two hours the mixture is filtered
  2. washthe solid washed with diethyl ether
  3. washThe combined ethereal layers were washed with water, 10% sodium hydroxide in water solution, water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue is treated with a diethyl ether solution of hydrogen chloride
  7. customthe resultant precipitate is recrystallized from a methanol/ethyl acetate mixture

Sources & evidence

ORD record
ord-7984877a6f6246fc8d7651afbccb70f6
Source dataset
uspto-grants-1984_07
Patent number
US04460600

Reaction notes

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