Dimethylformamide → HCID 12962160, compound
Reaction equation
[H-].[Na+].[C:3]([CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)#[N:4].Cl.[CH3:21][N:22]([CH3:27])[CH:23](C)[CH2:24]Cl.[CH3:28]N(C=O)C>>[C:3]([C:5]1([CH2:28][CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)#[N:4]Participants
Procedure
Sodium hydride (4.28 g; 0.18 mole) is added portionwise with cooling (5°-10° C.) under nitrogen to a solution of 11-cyano-6,11-dihydrodibenz[b,e]oxepin (16.0 g; 0.72 mole), of Example 1A, in dry DMF (320 ml) and stirred at ambient temperature for 11/2 hours. At this time, 2-dimethylaminopropyl chloride hydrochloride (15.92 g; 0.10 mole) is added portionwise while maintaining the temperature below 10° C. Upon completion of the addition, stirring is continued at 80° C. for 20 hours. The reaction mixture is cooled, poured into 2 liters of ice water and extracted with ether. The ether is back extracted with 2 N HCl and the acidic washes combined and made basic with potassium carbonate. After extraction with ether and drying (K2CO3) the ether is removed in vacuo to give a solid. Trituration with hexane and drying provides 7.0 g (32%) of a solid (m.p. 112°-114° C.) of 11-cyano-11-[3-(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin.
Workup
- temperaturewhile maintaining the temperature below 10° C
- additionUpon completion of the addition
- temperatureThe reaction mixture is cooled
- extractionextracted with ether
- extractionThe ether is back extracted with 2 N HCl
- extractionAfter extraction with ether
- dry with materialdrying (K2CO3) the ether
- customis removed in vacuo
- customto give a solid
- dry with materialTrituration with hexane and drying
Sources & evidence
- ORD record
- ord-1019637051a34d4cac7476ca1ee0cd18
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04335122
Reaction notes
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