Ammonia → HCID 13342875, compound

HRID 1262864Notes

Reaction equation

HRID 1262864 reaction equation
[CH2:1]([N:4]([CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH2:9]1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].N.[Na].CO>O1CCCC1.C(O)(C)C>[CH3:19][O:18][C:13]1[CH2:14][C:15]2[CH2:16][CH2:17][CH:8]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH3:7])[CH2:9][C:10]=2[CH2:11][CH:12]=1

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 887MethanolHCID 5360545SodiumHCID 12741429HCID 12741429, compound

Product 1

HCID 13342875HCID 13342875, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dipropyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine (17.6 g, 0.067 mole) in tetrahydrofuran (188 mL) and isopropanol (188 mL) was added with stirring to liquid ammonia (500 mL) cooled by a dry ice-isopropanol bath. Sodium (29.4 g, 1.3 g-atom) was added in small pieces over 0.5 hr. After the blue colour disappeared (ca. 2 hr), methanol (120 mL) was added and the ammonia was allowed to evaporate after removal of the cooling bath. The residue was diluted with water (1000 mL) and extracted three times with diethyl ether. The ether extracts were dried (MgSO4) and concentrated, giving a yellow oil (15.8 g) of 1,2,3,4,5,8-hexahydro-6-methoxy-N,N-dipropyl-2-naphthalenamine, NMR (CDCl3) δ 0.85 (t, 6H), 3.5 (s, 3H) and 4.6 (m, 1H).

Workup

  1. temperaturecooled by a dry ice-isopropanol bath
  2. additionwas added
  3. customto evaporate
  4. customafter removal of the cooling bath
  5. additionThe residue was diluted with water (1000 mL)
  6. extractionextracted three times with diethyl ether
  7. dry with materialThe ether extracts were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c127d593a3754d9689df3ea40a4d32fc
Source dataset
uspto-grants-1984_06
Patent number
US04454150

Reaction notes

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