Dimethylamine → HCID 22638783, compound

HRID 1836657Notes

Reaction equation

HRID 1836657 reaction equation
[S:1]1[CH:5]=[C:4]([C@@H:6]2[CH2:8][C@H:7]2[CH:9]=O)[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.[CH3:15][NH:16][CH3:17].C1COCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)C.Cl>[S:1]1[CH:5]=[C:4]([CH:6]2[CH2:8][CH:7]2[CH2:9][N:16]([CH3:17])[CH3:15])[C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86587688HCID 86587688, compound

Product 1

HCID 22638783HCID 22638783, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Trans-2-benzo[b]thiophen-3-yl-cyclopropanecarbaldehyde (202 mg, 1.0 mmol) was dissolved in 10 mL ethanol. To this solution was added a 2.0 M solution of dimethylamine in THF (5.0 mL, 10.0 mmol). After stirring for 15 min, sodium triacetoxyborohydride (850 mg, 4.0 mmol) was added and the reaction continued for 1 h. The reaction was diluted with 10 mL 0.1 N HCl, then solid sodium bicarbonate was added in portions to adjust pH to 7. The mixture was extracted with ethyl acetate (2×20 mL), and the organic extracts were pooled, washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by preparative reverse phase high-performance liquid chromatography afforded (2-benzo[b]thiophen-3-yl-cyclopropylmethyl)-dimethyl-amine (246 mg, 71%) as an oily trifluoroacetic acid salt. 1H NMR (500 MHz, d4-MeOH) 7.94 (1H, d, J=7.94 Hz), 7.86 (1H, d, J=7.93 Hz), 7.42 (1H, t, J=7.94), 7.37 (1H, t, J=7.94), 7.21 (1H, s), 3.44 (1H, dd, J=13.12, 6.71 Hz), 3.22 (1H, dd, J=13.12, 8.24 Hz), 2.97 (6H, s), 2.28 (1H, p, J=4.6 Hz), 1.56 (1H, m), 1.20 (2H, m). LC-MS: 1.10 min; 232.2 (MH)+.

Workup

  1. waitthe reaction continued for 1 h
  2. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative reverse phase high-performance liquid chromatography

Sources & evidence

ORD record
ord-0ed418df77ae4354bb9986889d940a70
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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