Methylamine → HCID 67125394, compound

HRID 1470756Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([NH2:24])[CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)[CH3:2].C1N=C[N:27]([C:30](N2C=NC=C2)=[O:31])[CH:26]=1.CN>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]3[CH:17]=[CH:18][C:19]([C@@H:22]([NH:24][C:30]([NH:27][CH3:26])=[O:31])[CH3:23])=[CH:20][CH:21]=3)[CH2:14][CH2:15]2)=[CH:8][CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To 100 mg (0.31 mmol) (S)-1-{4-[1-(4-ethoxy-phenyl)-piperidin-4-yl]-phenyl}-ethylamine (XIII.1) in 2 mL DMF, 87 μL (0.62 mmol) TEA and 52 mg (0.32 mmol) CDI are added at 0° C. and the mixture is stirred for 30 min at 0° C. Subsequently 48 mg (1.54 mmol) methylamine are added and stirring is continued for 1 h at 50° C. The mixture is filtered through basic aluminum oxide and concentrated in vacuo. The residue is purified using reversed phase column chromatography (water+0.15% NH4OH; acetone) and the corresponding fractions are concentrated to yield the desired product.

Workup

stirringstirring
waitis continued for 1 h at 50° C
filtrationThe mixture is filtered through basic aluminum oxide
concentrationconcentrated in vacuo
customThe residue is purified
concentrationthe corresponding fractions are concentrated

Sources & evidence

ORD record: ord-0c3c5781e05d4500b6c45048585df158
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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