Dimethylamine → 3-amino-N,N-dimethylbenzylamine

HRID 964635Notes

Reaction equation

HRID 964635 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=O)([O-])=O.[CH3:13][NH:14][CH3:15].Cl[Sn]Cl.C1COCC1>CCOC(C)=O>[CH3:13][N:14]([CH2:7][C:6]1[CH:5]=[C:4]([CH:12]=[CH:11][CH:10]=1)[NH2:1])[CH3:15]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8495Benzoyl chloride, 3-nitro-HCID 24479Stannous Chloride

Product 1

HCID 992943-amino-N,N-dimethylbenzylamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with 3-[(dimethylamino)methyl]aniline to generate the title compound. The 3-[(dimethylamino)methyl]aniline was prepared by treatment of commercial 3-nitrobenzoyl chloride with dimethylamine followed by sequential reduction with SnCl2 in EtOAc at 20° C. for 18 hours and then BH3 /THF.

Sources & evidence

ORD record
ord-4c04715ff0df46ac889457eb0edb1fea
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

Loading…