Triethylamine → N-[(4-Chlorophenyl)-(3-nitrophenyl)methyl}-N-[(R)-1-(3-fluorophenyl)ethyl]amine

HRID 2269489Notes

Reaction equation

HRID 2269489 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[F:20][C:21]1[CH:22]=[C:23]([C@H:27]([NH2:29])[CH3:28])[CH:24]=[CH:25][CH:26]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:29][C@@H:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[CH:22]=2)[CH3:28])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 7673464-Chloro-3'-nitrobenzophenoneHCID 5003444Sodium cyanoborohydrideHCID 45072322(R)-1-(3-Fluorophenyl)ethylamine hydrochloride

Product 1

HCID 70190114N-[(4-Chlorophenyl)-(3-nitrophenyl)methyl}-N-[(R)-1-(3-fluorophenyl)ethyl]amineYield 96.6%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a similar procedure to that described in Example (1a), 880 mg of 4-chlorophenyl 3-nitrophenyl ketone, 886 mg of (R)-1-(3-fluorophenyl)ethylamine hydrochloride, 2.58 ml of triethylamine, 0.44 ml of titanium tetrachloride, 890 mg of sodium cyanoborohydride and 0.29 ml of acetic acid were reacted, to obtain 1.25 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e213ade1e1fd49218008440efc1d9440
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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