Sodium Sulfate → 1-[3-(4-Methylpiperazin-1-yl)-2,3,4,5-tetrahydrooxepin-3-yl]methanamine
Reaction equation
[C:1]([C:3]1([N:10]2[CH2:15][CH2:14][N:13]([C:16](OCC)=O)[CH2:12][CH2:11]2)[CH2:9][CH2:8][CH:7]=[CH:6][O:5][CH2:4]1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:16][N:13]1[CH2:12][CH2:11][N:10]([C:3]2([CH2:1][NH2:2])[CH2:9][CH2:8][CH:7]=[CH:6][O:5][CH2:4]2)[CH2:15][CH2:14]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl 4-(3-cyano-2,3,4,5-tetrahydrooxepin-3-yl)piperazine-1-carboxylate (320 mg, 1.146 mmole) in dry THF (5 ml) was added LAH (1.75 ml, 3.50 mmole) at 0° C. After 30 min the mixture was warmed to RT. After 16 hr the mixture was cooled to 0° C. and slowly quenched with 2M NaOH until gas evolution had ceased and a fine white precipitate formed. Anhydrous Na2SO4 was added and the mixture stirred for 15 min. The slurry was filtered through a pad of Celite washing with THF. The filtrate was concentrated to give the title compound as a clear oil (250 mg, 97%) which was used in the next step without purification. 1H-NMR (CDCl3, 500 MHz) d 6.23 (d, J=6.83 Hz, 1 H), 4.60 (m, 1 H), 4.11 (dd AB, J=12.46 and 58.83 Hz, 2 H), 2.77 (s, 2 H), 2.70 (m, 4 H), 2.43 (m, 4 H), 2.27 (s, 3 H), 2.13 (m, 4 H).
Workup
- temperatureAfter 16 hr the mixture was cooled to 0° C.
- customslowly quenched with 2M NaOH until gas evolution
- customa fine white precipitate formed
- filtrationThe slurry was filtered through a pad of Celite
- washwashing with THF
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-385f46438cac4c24a644b42e00c74b5a
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389720B2
Reaction notes
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