4-Nitrobenzyl chloride → 4-(Pyrrolidin-1-ylmethyl)aniline

HRID 2105300Notes

Reaction equation

HRID 2105300 reaction equation
C([C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1)#C.ClC1C(C#N)=[C:15]([NH:19][C:20]2C=CC=[C:22]([C:26]#C)[CH:21]=2)N=CN=1.C(C1C=C(N2C3C4C(=C(C(O)=O)SC=4N=CN=3)NC2=O)C=CC=1)#C.N1CCCC1.ClCC1C=CC([N+]([O-])=O)=CC=1>>[N:19]1([CH2:15][C:8]2[CH:3]=[CH:4][C:5]([NH2:9])=[CH:6][CH:7]=2)[CH2:20][CH2:21][CH2:22][CH2:26]1

Participants

6

Reactant 5

HCID 74824-Nitrobenzyl chlorideHCID 31268PyrrolidineHCID 104682Benzenamine, 3-ethynyl-HCID 86616381HCID 86616381, compoundHCID 86616382HCID 86616382, compound

Product 1

HCID 7768524-(Pyrrolidin-1-ylmethyl)aniline

Procedure

Using the procedure of Example 1, 3-ethynyl-phenylamine Compound 54a was used in place of 3-chloro-4-fluoro-phenylamine Compound 1e to prepare 4-chloro-6-(3-ethynyl-phenylamino)-pyrimidine-5-carbonitrile Compound 54b. MS 255 (MH+). Using the procedure of Example 1, Compound 54b was used in place of Compound 1f to prepare 5-(3-ethynyl-phenyl)-4-oxo-4,5-dihydro-3H-1-thia-3,5,6,8-tetraaza-acenaphthylene-2-carboxylic acid Compound 54c. MS 335 (M−). Using the procedure of Example 1, pyrrolidine was used in place of piperidine and combined with 1-chloromethyl-4-nitro-benzene Compound 1i and taken forward to provide 4-pyrrolidin-1-ylmethyl-phenylamine Compound 54e. MS 177 (MH+). Using the procedure of Example 2, Compound 54c was used in place of Compound 40 and Compound 54e was used in place of 3,4-dimethoxy-phenylamine Compound 2c to give Compound 15. MS 495 (MH+).

Sources & evidence

ORD record
ord-c2ada36cbf194e808109b52509e7627f
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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