Ammonia → 6-(Dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-ol

HRID 883268Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([N:13]([CH3:15])[CH3:14])[CH2:8]2.B(Br)(Br)Br.N>C(Cl)Cl>[CH3:14][N:13]([CH3:15])[CH:7]1[CH2:6][CH2:5][C:4]2[C:3]([OH:2])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

N-(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N,N-dimethylamine (8.86 g, 43.156 mmol) was dissolved in CH2Cl2 (200 mL), cooled to 0° C. and BBr3 (1.0 M in CH2Cl2, 51.8 mL, 51.788 mmol) was added over a period of 20 min. The reaction mixture was allowed to reach r.t. while stirring overnight (ca. 14 h). The mixture was cooled again to 0° C., NH3 aq. (25%, 50 mL) was added slowly and the mixture was stirred at 0° C. for 15 min. The salts were filtered off, layers were separated and the aqueous phase was extracted with CH2Cl2 (4×40 mL). All organic phases were combined, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue (6.99 g) was purified by flash chromatography on silica gel (30:70:2-100:0:2 AcOEt/Hexane/Et3N and 30:70:2 AcOEt/Hexane/Et3N-90:10:2 AcOEt/MeOH/Et3N) affording 2.80 g of the title compound (Rf=0.3 (AcOEt/Hexane/Et3N 10:10:2), off-white solid, 34% yield).

Workup

customto reach r.t.
temperatureThe mixture was cooled again to 0° C.
stirringthe mixture was stirred at 0° C. for 15 min
filtrationThe salts were filtered off
customlayers were separated
extractionthe aqueous phase was extracted with CH2Cl2 (4×40 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue (6.99 g) was purified by flash chromatography on silica gel (30:70:2-100:0:2 AcOEt/Hexane/Et3N and 30:70:2 AcOEt/Hexane/Et3N-90:10:2 AcOEt/MeOH/Et3N)

Sources & evidence

ORD record: ord-2cc552be7c0048f5b65f4d20f84cbc36
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236845B2

Reaction notes

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