Benzaldehyde → N-(4-Bromobenzyl)-4-fluoro-N-isopropylbenzenamine

HRID 717664Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][CH:7]([CH3:9])[CH3:8])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.Cl.N(CC(O)=O)C.C(=O)C1C=CC=CC=1>>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:15][CH:14]=1

Participants

Reactant 4

HCID 240Benzaldehyde

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)

HCID 707414-Bromobenzaldehyde

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-

Product 1

HCID 66614972N-(4-Bromobenzyl)-4-fluoro-N-isopropylbenzenamineYield 93%

Procedure

When the product of Step A and 4-bromobenzaldehyde were substituted for sarcosine hydrochloride salt and 4-(5-(((4-fluorophenyl)) isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde, respectively, in Example 22, Step C, the similar process afforded the title compound in 93% yield, as a pale paste. 1H-NMR (CDCl3) 7.39 (d, 2H, J=8.18 Hz); 7.14 (d, 2H, J=8.08 Hz); 6.91-6.81 (m, 2H); 6.62-6.57 (m, 2H); 4.26 (s, 2H); 4.11-4.04 (m, 1H); 1.18 (d, 2H, J=5.34 Hz).

Sources & evidence

ORD record: ord-5b437486579f40099c7793c29f5c5414
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193716B2

Reaction notes

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