Triethylamine → N-[(R)-1-(3-Fluorophenyl)ethyl]-N-[(3-nitrophenyl)phenylmethyl]amine

HRID 2269520Notes

Reaction equation

HRID 2269520 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:20]=[C:21]([C@H:25]([NH2:27])[CH3:26])[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:18][C:19]1[CH:20]=[C:21]([C@H:25]([NH:27][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:26])[CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 752433-NitrobenzophenoneHCID 5003444Sodium cyanoborohydrideHCID 7016260(R)-1-(3-fluorophenyl)ethanamine

Product 1

HCID 70189344N-[(R)-1-(3-Fluorophenyl)ethyl]-N-[(3-nitrophenyl)phenylmethyl]amineYield 94%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

Following a procedure similar to that described in Example (1a), 1.0 g of 3-nitrophenyl phenyl ketone, 1.12 g of (R)-1-(3-fluorophenyl)ethylamine, 3.27 ml of triethylamine, 0.56 ml of titanium tetrachloride, 1.13 g of sodium cyanoborohydride and 0.37 ml of acetic acid were reacted, to obtain 1.45 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b54becdcd2e647658cff898293330a00
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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