Triethylamine → N-[(R)-1-(3,4-difluorophenyl)ethyl]-N-[(3-nitrophenyl)phenylmethyl]amine

HRID 2269522Notes

Reaction equation

HRID 2269522 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.Cl.[F:19][C:20]1[CH:21]=[C:22]([C@H:27]([NH2:29])[CH3:28])[CH:23]=[CH:24][C:25]=1[F:26].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[F:19][C:20]1[CH:21]=[C:22]([C@H:27]([NH:29][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)[CH3:28])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 752433-NitrobenzophenoneHCID 5003444Sodium cyanoborohydrideHCID 45072357(R)-1-(3,4-Difluorophenyl)ethanamine hydrochloride

Product 1

HCID 70189165N-[(R)-1-(3,4-difluorophenyl)ethyl]-N-[(3-nitrophenyl)phenylmethyl]amineYield 87%

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, 1.24 g of (R)-1-(3,4-difluorophenyl)ethylamine hydrochloride, 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 1.41 g of the title compound as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-080291af66664bfd92723a32c4324223
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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