Triethylamine → 8-(1H-Indene-2-carbonyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

HRID 2072504Notes

Reaction equation

HRID 2072504 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C(N(CC)CC)C.ClC(OCC)=O.[C:26]1([N:32]2[C:36]3([CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[C:35](=[O:42])[NH:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1.CN1CCOCC1>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([N:39]1[CH2:38][CH2:37][C:36]2([N:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:33][NH:34][C:35]2=[O:42])[CH2:41][CH2:40]1)=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 5754641H-Indene-2-carboxylic acid

Product 1

HCID 214082488-(1H-Indene-2-carbonyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

Reagents, catalysts & solvents 2

HCID 79724-MethylmorpholineCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Indene-2-carboxylic acid (12.8g) is dissolved in dry tetrahydrofuran (300 ml), cooled to 0° C, treated with N-methylmorpholine (40 drops), triethylamine (12 ml) and ethyl chloroformate (8.6g) and stirred for 30 minutes. To this mixture is added a suspension of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (20.0g) in dry tetrahydrofuran (200 ml) and the mixture is stirred at 0° C for 30 minutes. The mixture is allowed to warm to room temperature and stirred for 16 hours. The precipitated solids are filtered off, washed with additional tetrahydrofuran, and the filtrate is concentrated. The semi-solid residue is dissolved in chloroform, washed with water and saturated sodium bicarbonate solution, dried, and concentrated to give the crude product.

Workup

  1. additionTo this mixture is added
  2. stirringthe mixture is stirred at 0° C for 30 minutes
  3. temperatureto warm to room temperature
  4. stirringstirred for 16 hours
  5. filtrationThe precipitated solids are filtered off
  6. washwashed with additional tetrahydrofuran
  7. concentrationthe filtrate is concentrated
  8. dissolutionThe semi-solid residue is dissolved in chloroform
  9. washwashed with water and saturated sodium bicarbonate solution
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-eafd6a170e7c408f9703229bf0c3c81c
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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