Triethylamine → HCID 67258220, compound

HRID 1967893Notes

Reaction equation

HRID 1967893 reaction equation
[CH2:1]([O:3][CH:4]([O:14][CH2:15][CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH3:13])=[CH:7][CH:6]=1)[CH3:2].C(N(CC)CC)C.[C:24](Cl)(=[O:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[CH2:15]([O:14][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH3:13])[C:24](=[O:33])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:7][CH:6]=1)[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 12027889HCID 12027889, compound

Product 1

HCID 67258220HCID 67258220, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-(4-(diethoxymethyl)phenyl)-N-methylmethanamine (1.1 g, 4.9 mmol) and triethylamine (0.75 g, 7.35 mmol) in anhydrous dichloromethane (10 mL) was added benzyl carbonochloridate (1.0 g, 5.88 mmol) at 0° C. After the addition, the mixture was allowed to stir at room temperature overnight. The mixture was diluted with dichloromethane (50 mL), washed with water (50 mL×3), brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to give crude product which was purified by chromatography (silica gel, petroleum ether/ethyl acetate=100:1 to 20:1) to give benzyl 4-(diethoxymethyl)benzyl(methyl)carbamate (1.0 g, yield 57% for two steps) as a light yellow oil. 1H-NMR (400 MHz, CDCl3) δ: 3.82 (s, br 1H), 5.19 (s, 3H), 6.91-6.95 (m, 1H), 7.32-7.36 (m, 2H); LC-MS (ESI) m/z: 358 (M+1)+.

Workup

  1. additionAfter the addition
  2. washwashed with water (50 mL×3), brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified by chromatography (silica gel, petroleum ether/ethyl acetate=100:1 to 20:1)

Sources & evidence

ORD record
ord-20cfd17011f0425e9f0a729ec180587f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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