HCID 20511351, compound → HCID 10800464, compound

HRID 1164502Notes

Reaction equation

HRID 1164502 reaction equation
Br.[CH2:2]([N:5]([CH2:20][CH2:21][CH3:22])[CH:6]1[CH2:15][C:14]2[CH:13]=[C:12]([NH:16]C(=O)C)[CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7]1)[CH2:3][CH3:4]>O.[OH-].[Na+]>[CH2:20]([N:5]([CH2:2][CH2:3][CH3:4])[CH:6]1[CH2:7][CH2:8][C:9]2[C:14](=[CH:13][C:12]([NH2:16])=[CH:11][CH:10]=2)[CH2:15]1)[CH2:21][CH3:22]

Participants

4

Reactant 1

HCID 20511351HCID 20511351, compound

Product 1

HCID 10800464HCID 10800464, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of N-[7-(dipropylamino)-5,6,7,8-tetrahydro-2-naphthalenyl]-acetamide hydrobromide (3.0 g, 8.1 mmoles) in water was treated in 1N sodium hydroxide (100 ml) and the resulting free base was extracted in benzene. The solvent was evaporated and the residue was heated at reflux in 2N hydrochloric acid (37 ml) for 2 hr. After cooling, the solution was basified with 1N sodium hydroxide and extracted three times with benzene. The organic extracts were dried (MgSO4) and concentrated to afford a red oil (1.76 g) of 1,2,3,4-tetrahydro-N2, N2 -dipropyl-2,7-naphthalenediamine: NMR (CDCl3) δ 0.85 (t, 6H), 1.42 (m, 6H), 2.42 (t, 4H), 2.70 (m, 4H), 6.35 (m, 2H) and 6.80 (d, 1H). The di-(Z)-2-butenedioate salt was prepared in acetone and diethyl ether, and crystallized from methanol-diethyl ether: mp 124°-126° C. and Anal. Calcd for C 16 H26N2.2C4H4O2 : C, 60.23%; H, 7.16%, N, 5.85%; and Found: C, 60.45%; H, 7.21%; N, 5.88%.

Workup

  1. extractionthe resulting free base was extracted in benzene
  2. customThe solvent was evaporated
  3. temperaturethe residue was heated
  4. temperatureat reflux in 2N hydrochloric acid (37 ml) for 2 hr
  5. temperatureAfter cooling
  6. extractionextracted three times with benzene
  7. dry with materialThe organic extracts were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b6f2ddf525e749f09f92aba517df8b80
Source dataset
uspto-grants-1983_01
Patent number
US04370341

Reaction notes

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