Triethylamine → N-[1-(3,4-Difluorophenyl)ethyl]-N-[(2-fluoro-5-nitrophenyl)-(4-methoxyphenyl)methyl]amine

HRID 2269463Notes

Reaction equation

HRID 2269463 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[F:20])=O)=[CH:5][CH:4]=1.Cl.[F:22][C:23]1[CH:24]=[C:25]([CH:30]([NH2:32])[CH3:31])[CH:26]=[CH:27][C:28]=1[F:29].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:22][C:23]1[CH:24]=[C:25]([CH:30]([NH:32][CH:9]([C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[F:20])[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:31])[CH:26]=[CH:27][C:28]=1[F:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 18347113Benzenemethanamine, 3,4-difluoro-α-methyl-, hydrochloride (1:1)HCID 701897642-Fluoro-5-nitrophenyl 4-methoxyphenyl ketone

Product 1

HCID 18334198N-[1-(3,4-Difluorophenyl)ethyl]-N-[(2-fluoro-5-nitrophenyl)-(4-methoxyphenyl)methyl]amineYield 68.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 828 mg of 2-fluoro-5-nitrophenyl 4-methoxyphenyl ketone, 1.16 g of 1-(3,4-difluorophenyl)ethylamine hydrochloride, 2.52 ml of triethylamine, 0.40 ml of titanium tetrachloride, 840 mg of sodium cyanoborohydride and 0.62 ml of acetic acid were reacted, to obtain 860 mg of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ee39a17ebafd4c8897483ad36ca76c64
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

Loading…