N-Methylbenzylamine → HCID 71613321, compound

HRID 1053572Notes

Reaction equation

HRID 1053572 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[CH3:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:14]([N:13]([CH3:12])[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 81531DiisopropylethylamineHCID 128339324-(2-Bromoethoxy)phenol

Product 1

HCID 71613321HCID 71613321, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Compound 8a (0.25 g, 1.15 mmol) and N-methyl-1-phenylmethanamine (0.18 g, 1.38 mmol) were stirred in acetonitrile (12.0 mL) for 20 mins before diisopropylethylamine was added (0.40 mL, 2.30 mmol) dropwise. After the addition was complete, the reaction was stirred at 60° C. for 12 hours and monitored by TLC. The reaction mixture was concentrated, purified by column chromatography to isolate the compound 8 as a brownish oil (0.20 g, 0.77 mmol, 67% yield). MS (ESI, positive) m/z calcd. for C16H20NO2 [M+H]+: 258.15, found: 257.98. 1H NMR (CDCl3, 400 MHz) δ 7.30-7.37 (m, 4H), 6.74-6.82 (m, 5H), 4.05 (t, J=6 Hz, 2H), 3.78 (s, 1H), 3.645 (s, 2H), 2.83 (t, J=6.0 Hz, 2H).

Workup

  1. additionwas added (0.40 mL, 2.30 mmol) dropwise
  2. additionAfter the addition
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-0df38df3006e4f3cb679b28605be06cb
Source dataset
uspto-grants-2016_07
Patent number
US09394233B2

Reaction notes

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