Hydrochloric Acid → 1-Aminomethyl-3,4-dihydronaphthalene

HRID 467040Notes

Reaction equation

HRID 467040 reaction equation
[NH2:1][CH2:2][C:3]1(O)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.Cl.C(OCC)C>CC(O)C>[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol2×

Product 1

HCID 129148601-Aminomethyl-3,4-dihydronaphthaleneYield 59%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-Aminomethyl-1-hydroxy-1,2,3,4-tetrahydronaphthalene, the product of Example 7, was refluxed in a 2N solution of hydrogen chloride in 2-propanol (250 mL) for 5 hours. A portion of the 2-propanol was removed under reduced pressure to give a slurry. Diethyl ether was added to precipitate the hydrochloride salt. The resulting suspension was then filtered. The filter cake was then recrystallized from methanol/diethyl ether to give 16.18 g (59% yield based on 1,2,3,4-tetrahydronaphthalene-1-one) of the desired product as a light tan solid; 1H NMR (CD3OD) δ 2.31-2.40 (m, 2H), 2.80 (t, 2H, J=8 Hz), 4.0 (s, 2H), 6.26 (t, 1H, J=4.5 Hz), 7.19-7.29 (m, 4H).

Workup

  1. customA portion of the 2-propanol was removed under reduced pressure
  2. customto give a slurry
  3. customto precipitate the hydrochloride salt
  4. filtrationThe resulting suspension was then filtered
  5. customThe filter cake was then recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-6d116543b3c7424d94df08ca4c8c9142
Source dataset
uspto-grants-1992_10
Patent number
US05158948

Reaction notes

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