Hydrochloric Acid → (4-(tetrahydro-2H-pyran-4-yl)phenyl)methanamine

HRID 1961440Notes

Reaction equation

HRID 1961440 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]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 666329764-(Tetrahydro-2H-pyran-4-yl)benzonitrile

Product 1

HCID 66632713(4-(tetrahydro-2H-pyran-4-yl)phenyl)methanamine

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 3283Diethyl EtherSolvent

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

  1. customto remove the Boc group
  2. additionThe crude was treated with aqueous NaHCO3
  3. extractionextracted with CH2Cl2
  4. customto afford
  5. customafter drying
  6. 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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