Dimethylformamide → 1-(3-Methoxypropyl)piperazine
Reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].C([N:8]([CH2:11]C)[CH2:9]C)C.C1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH3:17][O:16][CH2:15][CH2:14][CH2:4][N:2]1[CH2:1][CH2:9][NH:8][CH2:11][CH2:3]1Participants
Procedure
In a similar manner to Step 1 of Example 224, bromide was obtained from (E)-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}methanol (0.30 g, 1.0 mmol) obtained in Step 1 of Example 306, carbon tetrabromide (1.0 g, 3.1 mmol) and triphenylphosphine (0.80 mg, 3.1 mmol). Further, in a similar manner to Step 2 of Example 224, a crude product was obtained from DMF (6.0 mL) and 1-(3-methoxypropyl)piperazine (0.48 g, 3.1 mmol), triethylamine (0.43 mL, 3.1 mmol) and THF (6.0 mL), and the product was used for next step without isolation. In a similar manner to Example 2, the crude product was treated with tin (0.39 g, 3.3 mmol), concentrated hydrochloric acid (1.4 mL) and ethanol (8.9 mL), to obtain (E)-2-[2-(1H-indazol-3-yl)vinyl]-5-[4-(3-methoxypropyl)piperazin-1-ylmethyl]phenylamine (0.34 g, 81%).
Sources & evidence
- ORD record
- ord-353383af739c4a709e01c45d4da5e203
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07605272B2
Reaction notes
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