Hydrochloric Acid → (6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanamine

HRID 6730

Reaction equation

HRID 6730 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.CN.[C:16]([BH3-])#[N:17].[Na+].Cl>CO.O.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:16][NH2:17])[CH2:7][CH2:6]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 15718592(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanamineYield 41.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 6-methoxy-3,4-dihydro-1H-naphthalen-2-one (176 mg, Aldrich, U.S.A.), acetic acid (0.57 mL), methylamine (2.0 M in tetrahydrofuran, 5.0 mL), and sodium cyanoborohydride (64 mg) was stirred in 5 mL methanol for 20 h. The solution was acidified to a pH<2 with concentrated hydrochloric acid, diluted with water to a volume of 50 mL, and extracted with 50 mL of dichloromethane. The aqueous phase was made basic (pH>10) by the addition of 1 M sodium hydroxide and extracted with two 50 mL aliquots of dichloromethane. The basic dichloromethane extracts were dried in vacuo to yield 80 mg of (6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methylamine.

Workup

  1. extractionextracted with 50 mL of dichloromethane
  2. additionby the addition of 1 M sodium hydroxide
  3. extractionextracted with two 50 mL aliquots of dichloromethane
  4. dry with materialThe basic dichloromethane extracts were dried in vacuo

Sources & evidence

ORD record
ord-b0f2e62aef4e412897ab38669bbf8635
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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