Dimethylamine → Hydrochloric Acid

HRID 1096732Notes

Reaction equation

HRID 1096732 reaction equation
[C:1]1([C:11]23[CH2:16][CH:15]2[C:14](=O)[CH2:13][CH2:12]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:18][NH:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:35]C(Cl)C>C(=O)(O)[O-].[Na+]>[ClH:35].[CH3:18][N:19]([CH3:20])[CH:14]1[CH2:13][CH2:12][C:11]2([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[CH:15]1[CH2:16]2.[ClH:35]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59779131HCID 59779131, compound

Product 2

HCID 313Hydrochloric AcidHCID 66781757HCID 66781757, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

5-Naphthalen-1-yl-bicyclo[3.1.0]hexan-2-one (0.25 g, 1.13 mmol) in dichloroethane (10 mL) and dimethylamine (2M solution in tetrahydrofuran, 5.62 mL, 11.25 mmol, 10 eq.) was treated with sodium triacetoxyborohydride (0.24 g, 1.13 mmol) at room temperature. The reaction mixture was stirred for 19 h and concentrated to afford an oily residue. The resulting residue was diluted with saturated aqueous sodium bicarbonate (50 mL), extracted with dichloromethane (3×100 mL) and the combined organics were dried over potassium carbonate, filtered and concentrated in vacuo. The oil was dissolved in diethyl ether (10 mL) and the HCl salt was formed by slowly adding HCl (1M in diethyl ether, 1 mL). The slurry was stirred for 0.5 h before filtration. The solid pale brown solid was rinsed with diethyl ether and the compound was transferred to a vacuum oven for drying for 12 h to afford the desired compound as a brown solid. (0.074 g, 23%). 1H NMR (400 MHz, CD3OD) δ ppm. 1.17-1.44 (3H, m, 3×CH), 1.76-1.83 (2H, m, CH2), 1.94-2.06 (2H, m, CH2), 2.40 (3H, s, CH3), 2.42 (3H, s, CH3), 3.09-3.14 (1H, m, CH), 7.37-7.57 (4H, m, Ar), 7.71 (1H, d, J 8.0 Hz, ArH), 7.85 (1H, d, J 8.0 Hz, ArH), 8.26-8.28 (1H, d, J 7.6 Hz, ArH). 13C NMR (400 MHz, CD3OD); δ ppm 12.08 (s, 1C), 24.11 (s, 1C), 24.75 (s, 1C), 33.01 (s, 1C), 33.43 (s, 1C), 41.57 (s, 1C), 42.06 (s, 1C), 70.09 (s, 1C), 124.12 (s, 1C), 125.24 (s, 1C), 125.46 (s, 1C), 125.77 (s, 1C), 127.61 (s, 1C), 128.56 (s, 1C), 132.27 (s, 1C), 134.17 (s, 1C), 138.32 (s, 1C). LCMS (M+1) 252.

Workup

  1. concentrationconcentrated
  2. customto afford an oily residue
  3. extractionextracted with dichloromethane (3×100 mL)
  4. dry with materialthe combined organics were dried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe oil was dissolved in diethyl ether (10 mL)

Sources & evidence

ORD record
ord-390a0ef151224cecb9defecc27ffeb1d
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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