Ammonium Hydroxide → 2-Amino-6-(4-pyrrolidin-1-ylmethylphenoxy)pyridine

HRID 460216Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[N:3]=1.[NH4+:21].[OH-]>[Cl-].[Na+].O>[NH2:21][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-6-(4-pyrrolidin-1-ylmethylphenoxy)pyridine (20 g) and Cu powder (1 g) in concentrated NH4OH (250 mL, aq) and IpOH (60 mL) was heated at 100° C. in a sealed flask for 48 h. After cooling to RT, brine (300 mL) was added and the mixture was extracted with EtOAc (3×200 mL). The combined organic layer was washed with brine (300 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residues were filtered through silica gel pad eluting with MeOH/CH2Cl2 (5%). The filtrate was concentrated to dryness, then 50 mL of MeOH was added. After stirring for a while the solid was filtered to give the title compound. MS m/z: 270 (M+1). Calc'd for C16H19N3O-269.3

Workup

temperatureAfter cooling to RT
extractionthe mixture was extracted with EtOAc (3×200 mL)
washThe combined organic layer was washed with brine (300 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
filtrationThe residues were filtered through silica gel pad
washeluting with MeOH/CH2Cl2 (5%)
concentrationThe filtrate was concentrated to dryness
addition50 mL of MeOH was added
filtrationwas filtered

Sources & evidence

ORD record: ord-fb4dc28c1d28462ca9fa563561929f73
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196104B2

Reaction notes

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