5-Tetralinylamine → HCID 18932989, compound

HRID 1598471Notes

Reaction equation

HRID 1598471 reaction equation
[NH2:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[ClH:12].[Cl:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl>C(O)CCC>[ClH:13].[ClH:12].[C:2]1([N:1]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 166715-TetralinylamineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 18932989HCID 18932989, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 1-amino-5,6,7,8-tetrahydronaphthalene (2.44 g, 16.60 mmol) and bis-(2-chloroethyl)amine hydrochloride (2.69 g, 15.09 mmol) in n-butanol (15 mL) was heated at reflux under nitrogen for 3 d. The reaction was cooled to 20° C. The white precipitate was collected by filtration and washed with n-butanol, then dried under vacuum. The title compound was obtained as a white solid (1.64 g). NMR (300 MHz, CD3OD) δ 7.1 (1H, t, J=8 Hz), 6.9 (1H, d, J=8 Hz), 6.15 (1H, d, J=8 Hz), 3.35 (4H, m), 3.1 (4H, m), 2.75 (4H, m), 1.8 (4m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 d
  3. filtrationThe white precipitate was collected by filtration
  4. washwashed with n-butanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d9dae55599024424aba499f8b8911b75
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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