Salicylamide → 8-[(2-Hydroxybenzoyl)aminomethyl]-2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione

HRID 1381949Notes

Reaction equation

HRID 1381949 reaction equation
Cl.[CH3:2][O:3][N:4]1[C:8](=[O:9])[CH2:7][C:6]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:5]1=[O:15].[C:16]([NH2:25])(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].[CH2:26](N(CC)CC)C>C(O)C>[OH:19][C:18]1[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=1[C:16]([NH:25][CH2:26][N:12]1[CH2:13][CH2:14][C:6]2([C:5](=[O:15])[N:4]([O:3][CH3:2])[C:8](=[O:9])[CH2:7]2)[CH2:10][CH2:11]1)=[O:24]

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 8471TriethylamineHCID 30882852,8-Diazaspiro(4,5)decane-1,3-dione, 2-methoxy-, monohydrochloride

Product 1

HCID 143718678-[(2-Hydroxybenzoyl)aminomethyl]-2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione.hydrochloride (0.55 g), salicylamide (0.32 g), p-formaldehyde (0.11 g) and triethylamine (2 ml) in ethanol (20 ml) was stirred for 15 hours at room temperature. Then, the solvent was evaporated off under reduced pressure, and the residual oily product was subjected to a silica gel column chromatography (eluent; ethyl acetate), and the solvent for the solution containing the desired product was evaporated off under reduced pressure. The residual solid was recrystallized from ethyl ether to obtain 0.52 g of colorless crystals, m.p. 96° to 99° C.

Workup

  1. customThen, the solvent was evaporated off under reduced pressure
  2. additionthe solvent for the solution containing the desired product
  3. customwas evaporated off under reduced pressure
  4. customThe residual solid was recrystallized from ethyl ether

Sources & evidence

ORD record
ord-3e3ea5c82e6b43b683e01ef68c0d40c1
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

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