Triethylamine → HCID 131713581, compound

HRID 1462458Notes

Reaction equation

HRID 1462458 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:12][CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[C@H:4]1[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([Cl:32])=[O:31])=[CH:28][CH:27]=1>CCOCC>[ClH:32].[Br:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([N:2]([CH3:1])[C@@H:3]2[CH2:12][CH2:11][CH2:10][C:5]3([O:6][CH2:7][CH2:8][O:9]3)[C@H:4]2[N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 71406928(6S,7R)-N-Methyl-6-(pyrrolidin-1-yl)-1,4-dioxaspiro[4.5]decan-7-amine

Product 1

HCID 131713581HCID 131713581, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 7.2 g (0.03 mole) of trans-(±)-1-[7-(methylamino)-1,4-dioxaspiro[4.5]dec-6-yl]pyrrolidine in 200 ml Et2O and 3.64 g (0.036 mole) of triethylamine was added a solution of 7.9 g (0.036 mole) of 4-bromobenzoyl chloride in 50 ml Et2O over thirty minutes under N2. After two hours the slurry was filtered and the salt washed with Et2O. The combined ethereal layers were washed with H2O, 10% NaOH, H2O, brine, dried (MgSO4) and concentrated in vacuo. The residue was treated with Et2O/HCl and the resultant precipitate recrystallized from MeOH/EtOAc to give 7.0 g, mp 218°-219° and 1.68 g, mp 212°-214° (56%) of the titled amide: mp 219-220.5. The nmr and ir spectra were in accord with the titled amino amide ketal.

Workup

  1. filtrationAfter two hours the slurry was filtered
  2. washthe salt washed with Et2O
  3. washThe combined ethereal layers were washed with H2O, 10% NaOH, H2O, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with Et2O/HCl
  7. customthe resultant precipitate recrystallized from MeOH/EtOAc

Sources & evidence

ORD record
ord-cd9c9cb9b42b4d988d27d81bec092751
Source dataset
uspto-grants-1984_07
Patent number
US04460600

Reaction notes

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