N,N,N',N',N'',N''-Hexamethylmethanetriamine → Benzyl 10-((dimethylamino)methylene)-9-oxo-3-azaspiro[5,5]undec-7-ene-3-carboxylate

HRID 1892613Notes

Reaction equation

HRID 1892613 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2([CH2:21][CH2:20][C:19](=[O:22])[CH:18]=[CH:17]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][N:24]([CH:26](N(C)C)N(C)C)[CH3:25]>C1(C)C=CC=CC=1>[CH3:23][N:24]([CH:26]=[C:20]1[CH2:21][C:14]2([CH2:13][CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:16][CH2:15]2)[CH:17]=[CH:18][C:19]1=[O:22])[CH3:25]

Participants

4

Reactant 2

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 23435732Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

Product 1

HCID 66835449Benzyl 10-((dimethylamino)methylene)-9-oxo-3-azaspiro[5,5]undec-7-ene-3-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-oxo-3-aza-spiro[5.5]undec-7-ene-3-carboxylic acid benzyl ester, Preparation I-IA-2 (15.4 g, 51 mmol) was dissolved in 180 mL toluene and tris(dimethylamino)methane (22.2 g, 27 mmol) was added. The reaction was heated to reflux for 5 hours and then allowed to cool to room temperature overnight. The reaction solution was concentrated in vacuo to provide the title compound (18.0 g, 100%): +APCI MS (M+H) 354.6; 1H NMR (400 MHz, CDCl3) δ ppm 7.49 (s, 1H), 7.28-7.40 (m, 5H), 6.59 (d, J=10.16 Hz, 1H), 8.01 (d, J=9.97 Hz, 1H), 5.13 (s, 2H), 3.52-3.66 (m, 2H), 3.39-3.52 (m, 2H), 3.07 (s, 6H), 2.74 (s, 2H), 1.58-1.73 (m, 2H), 1.41-1.58 (m, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction solution was concentrated in vacuo

Sources & evidence

ORD record
ord-89f68211cbf241a99175ef947dbe5871
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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