Benzylamine → Benzyl-(4pyrrolidin1-ylmethyl-phenyl)-amine

HRID 989268Notes

Reaction equation

HRID 989268 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:27]([NH:34][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 127380041-(4-Bromobenzyl)pyrrolidine

Product 1

HCID 9965193Benzyl-(4pyrrolidin1-ylmethyl-phenyl)-amine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of 4-bromobenzyl-pyrrolidine (1 equiv, 120 mg), Pd2(dba)3 (2.0% equiv, 9.15 mg), t-Bu3P (1.6% equiv, 1.6 mg), benzylamine (1 equiv, 53.6 mg) and NaOtBu3 (1.5 equiv, 72 mg) in toluene (5 mL) was heated at 70° C. for 8 h.

Sources & evidence

ORD record
ord-8cfca8e7f9ec40489ccd493084e74b70
Source dataset
uspto-grants-2003_10
Patent number
US06638967B2

Reaction notes

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