N-Methylbenzylamine → HCID 68827767, compound

HRID 1988066Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10]Cl.[CH3:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([N:13]([CH3:12])[CH2:10][CH2:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 7669N-Methylbenzylamine

HCID 27790271-bromo-2-(2-chloroethoxy)benzene

Product 1

HCID 68827767HCID 68827767, compound

Conditions

Temperature: 65 °C

Procedure

The title compound was prepared from N-benzyl-N-[2-(2-bromophenoxy)ethyl]methyl amine in a similar manner to Example 1 (a) except that after evaporation of the dimethoxyethane, the aqueous residue was extracted with DCM (100 ml). The latter was then extracted with 5% aqueous acetic acid, the acetic acid extracts adjusted to pH 8 with 10N potassium hydroxide solution and the resulting precipitate collected by filtration, washed with water and digested in methanol (5 ml), affording the title compound as a solid. MS 425 (M+H)+. 1H NMR (DMSO-D6) 2.2 (s, 3H), 2.9 (t, 2H), 3.55 (s, 2H), 4.25 (t, 2H), 6.8 (s, 2H), 7.0 (t, 1H), 7.1 (d, 1H), 7.2-7.3 (m, 7H), 7.6 (d, 2H), 7.8 (s, 1H), 11.0 (s, 1H). b) N-Benzyl-N-[2-(2-bromophenoxy)ethyl]methylamine This was prepared from l-bromo-2-(2-chloroethoxy)benzene and N-methyl benzylamine in a similar manner to Example (b) except that the mixture was stirred at 65° C. for 16 h. MS (ES) 320 (M+H)+. 1H NMR (CDCl3) 2.4 (s, 3H), 2.9 (t, 2H), 3.7 (s, 2H), 4.1 (t, 2H), 6.7-6.9 (m, 2H), 7.15-7.4 (m, 6H), 7.5 (d, 1H).

Sources & evidence

ORD record: ord-f05637c790534a7282d2982782ddfef2
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553868B2

Reaction notes

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