1-Pyrrolidineethanamine → N-benzyl-5-ethoxymethyl-2-methyl-N'-(2-pyrrolidin-1-yl-ethyl)-benzene-1,3-diamine

HRID 1667511Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][CH2:17][CH3:18])[CH:12]=[C:11](Br)[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[NH2:63][CH2:64][CH2:65][N:66]1[CH2:70][CH2:69][CH2:68][CH2:67]1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([CH2:15][O:16][CH2:17][CH3:18])[CH:12]=[C:11]([NH:63][CH2:64][CH2:65][N:66]2[CH2:70][CH2:69][CH2:68][CH2:67]2)[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of benzyl-(3-bromo-5-ethoxymethyl-2-methyl-phenyl)-amine (1.253 g, 3.749 mmol), xantphos (134 mg, 0.232 mmol), 1-(2-aminoethyl)pyrrolidine (0.71 mL, 5.639 mmol), Pd2(dba)3 (10 mg, 0.120 mmol), NaOtBu (658 mg, 6.847 mmol) and anhydrous dioxane (40 mL) was heated to 95° C. for 14 h. The reaction was cooled, filtered through celite, rinsed with EtOAc and concentrated. Chromatography (EtOAc/MeOH) afforded N-benzyl-5-ethoxymethyl-2-methyl-N′-(2-pyrrolidin-1-yl-ethyl)-benzene-1,3-diamine (810 g) as an orange liquid. m/z (M+1) 368.36.

Workup

temperatureThe reaction was cooled
filtrationfiltered through celite
washrinsed with EtOAc
concentrationconcentrated

Sources & evidence

ORD record: ord-016b1de1baf144018cd665299772ed79
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044041B2

Reaction notes

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