Hydrochloric Acid → (4-(tetrahydro-2H-pyran-4-yl)phenyl)methanamine
Reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].Cl>C(OCC)C.Cl[Ni]Cl>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][NH2:12])=[CH:13][CH:14]=2)[CH2:3][CH2:2]1Participants
6
Procedure
340 mg (1.82 mmol) 4-(tetrahydro-2H-pyran-4-yl)benzonitrile was reduced according to the general procedure with NiCl2 and NaBH4. The intermediate Boc-protected amine was treated with 2M HCl in diethyl ether to remove the Boc group. The crude was treated with aqueous NaHCO3 and extracted with CH2Cl2 to afford after drying and evaporation 234 mg (67%) of the title compound as an oil.
Workup
- customto remove the Boc group
- additionThe crude was treated with aqueous NaHCO3
- extractionextracted with CH2Cl2
- customto afford
- customafter drying
- customevaporation 234 mg (67%) of the title compound as an oil
Sources & evidence
- ORD record
- ord-cb02278ac7bc4603b1ee21a0a2d30466
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415333B2
Reaction notes
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