4-methoxy-N-ethylamphetamine → 1-(2-{Ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-one

HRID 10194Notes

Reaction equation

HRID 10194 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][CH2:13][CH3:14])[CH3:11])=[CH:5][CH:4]=1.[O:15]=[C:16]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]1[CH2:23][CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:13]([N:12]([CH:10]([CH3:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:24][CH2:23][N:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:16]1=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 857254-methoxy-N-ethylamphetamineHCID 5049666Sodium triacetoxyborohydrideHCID 62024269(2-Oxo-azepan-1-yl)acetaldehyde

Product 1

HCID 121126971-(2-{Ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-oneYield 91.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of [2-(4-methoxyphenyl)-1-methylethyl]ethylamine (0.53 g, 2.75 mmole), (2-oxo-azepan-1-yl)acetaldehyde (0.5 g, 3.2 mmole), and sodium triacetoxyborohydride (0.88 g, 4.1 mmole) in 1,2-dichloroethane (15 mL) was stirred at room temperature for 60 hours. The mixture was concentrated, and the residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL). The organic solution was extracted with 5% hydrochloric acid (20 mL), and the aqueous acidic phase was washed with diethyl ether and the pH was adjusted to 12 with 25% sodium hydroxide. The mixture was extracted with dichoromethane, and the organic phase was dried (sodium sulfate) and concentrated to give 1-(2-{ethyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethyl)-azepan-2-one 11 (0.84 g) as a viscous oil, which was converted to the dibenzoyl-L-tartrate salt, Anal.: Calcd. for C38H46N2O10: C, 66.07; H, 6.71; N, 4.06%. Found C, 64.69; H, 6.45; N, 3.90%.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between diethyl ether (50 mL) and saturated aqueous sodium bicarbonate (25 mL)
  3. extractionThe organic solution was extracted with 5% hydrochloric acid (20 mL)
  4. washthe aqueous acidic phase was washed with diethyl ether
  5. extractionThe mixture was extracted with dichoromethane
  6. dry with materialthe organic phase was dried (sodium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-31a4da783b4043c68d0b6b22af21068e
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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