HCID 11643172, compound → 4-[3-(Dimethylamino)propoxy]-3-fluoroaniline

HRID 1159935Notes

Reaction equation

HRID 1159935 reaction equation
FC1C=CC=C(F)C=1C(NC1C=CC=C(C2C(C3C=CN=C(NC4C=CC(OC[C@@H]5CCCN5C)=C(F)C=4)N=3)=C3C=CC=CN3N=2)C=1)=O.[F:49][C:50]1[CH:55]=[C:54]([N+:56]([O-])=O)[CH:53]=[CH:52][C:51]=1[O:59][CH2:60][CH2:61][CH2:62][N:63]([CH3:65])[CH3:64]>>[CH3:65][N:63]([CH3:64])[CH2:62][CH2:61][CH2:60][O:59][C:51]1[CH:52]=[CH:53][C:54]([NH2:56])=[CH:55][C:50]=1[F:49]

Participants

3

Reactant 2

HCID 11643172HCID 11643172, compoundHCID 595138233-(2-Fluoro-4-nitrophenoxy)-N,N-dimethyl-1-propanamine

Product 1

HCID 261901354-[3-(Dimethylamino)propoxy]-3-fluoroaniline

Procedure

In an analogous procedure to Example 125, 343 mg of the title compound was prepared from {3-[(2-fluoro-4-nitrophenyl)oxy]propyl}dimethylamine to give the desired intermediate as brown oil: 1H NMR (CDCl3, 400 MHz) δ 1.89-1.96 (m, 2H), 2.24 (s, 6H), 2.44 (t, 2H, J=7.1 Hz), 3.49 (brs, 2H), 3.99 (t, 2H, J=6.5 Hz), 6.36 (d, 1H, J=8.6 Hz), 6.45 (dd, 1H, J=12.6 and 2.7 Hz), and 6.81 (dd, 1H, J=9.0 and 9.0 Hz).

Sources & evidence

ORD record
ord-dd870de470c34c8aa2fb22754a88e93c
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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