Triethylamine → N-[(3-nitrophenyl)-(4-methoxyphenyl)methyl]-N-[1-(4-acetoxyphenyl)ethyl]amine

HRID 2269411Notes

Reaction equation

HRID 2269411 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=O)=[CH:5][CH:4]=1.Cl.[C:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([NH2:33])[CH3:32])=[CH:27][CH:26]=1)(=[O:23])[CH3:22].C(N(CC)CC)C.C([BH3-])#N.[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[N+:15]([C:11]1[CH:10]=[C:9]([CH:7]([C:6]2[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[NH:33][CH:31]([C:28]2[CH:29]=[CH:30][C:25]([O:24][C:21](=[O:23])[CH3:22])=[CH:26][CH:27]=2)[CH3:32])[CH:14]=[CH:13][CH:12]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydrideHCID 183471414-(1-Aminoethyl)phenyl acetate hydrochloride

Product 1

HCID 18347104N-[(3-nitrophenyl)-(4-methoxyphenyl)methyl]-N-[1-(4-acetoxyphenyl)ethyl]amineYield 26.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 176Acetic AcidSolvent

Procedure

In a similar manner to that described in Example (1a), 4-methoxy-3′-nitrobenzophenone (500 mg), 4-(1-aminoethyl)phenyl acetate hydrochloride (1.0 g), triethylamine (1.63 ml), titanium tetrachloride (0.26 ml), sodium cyanoborohydride (543 mg) and acetic acid (0.17 ml) were reacted, to afford the title compound (215 mg) as a yellow oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-3cc72937f138497686e986137029556f
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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