N,N-Dimethylcyclohexylamine → HCID 178478545, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].CN(C)C1CCCCC1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[NH:32]1[C:40](=O)[C:39]2[NH:38][N:37]=[N:36][C:35]=2[N:34]=[CH:33]1.[OH-].[Na+]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:40]2[C:39]3[NH:38][N:37]=[N:36][C:35]=3[N:34]=[CH:33][N:32]=2)[CH:6]=[CH:7][CH:8]=1Participants
6
Conditions
- Temperature
- 170 °C
Procedure
To 3-chloroaniline (0.39 ml, 3.6 mmol) in dry dimethylcyclohexylamine (0.55 ml, 3.6 mmol) was added phosphorus pentoxide (0.52 g, 3.6 mmol). After heating in a 170° C. oil bath for 0.5 hours, 8-azahypoxanthine (0.50 g, 3.6 mmol) was added and stirring continued at 170° C. for 23 hours. The mixture was cooled to ambient temperature and 2M NaOH was added until basic. The solids were filtered off and washed consecutively with H2O, CH2Cl2 and methanol. The resulting solid was dried in vacuo to afford the title compound as a tan powder (0.26 g. 29%). LC-MS: 247 (MH+); anal. RP18-HPLC RT: 3.76 min.
Workup
- temperatureThe mixture was cooled to ambient temperature
- filtrationThe solids were filtered off
- washwashed consecutively with H2O, CH2Cl2 and methanol
- customThe resulting solid was dried in vacuo
Sources & evidence
- ORD record
- ord-50ea603ffa454eb6955817115db070e1
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06395733B1
Reaction notes
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