Water → 8-(Bis(2-chlorophenyl)methyl)-3-(2-pyrimidinyl)-8-azabicyclo(3.2.1)octan-3-ol

HRID 2373538Notes

Reaction equation

Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][C:3]=1[C:8]1([OH:16])[CH2:14][CH:13]2[NH:15][CH:10]([CH2:11][CH2:12]2)[CH2:9]1.Br[CH:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25].C([O-])([O-])=O.[K+].[K+].O>CC#N>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[N:15]1[CH:13]2[CH2:12][CH2:11][CH:10]1[CH2:9][C:8]([C:3]1[N:4]=[CH:5][CH:6]=[CH:7][N:2]=1)([OH:16])[CH2:14]2

Participants

Conditions

Temperature: 22.5 °C

Procedure

Under N2, a well stirred mixture of 3-pyrimidin-2-yl-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (4.5 g, 14 mmol), 1,1′-(bromomethylene)bis(2-chlorobenzene) (5.0 g, 16 mmol) and K2CO3 (10.0 g, 72 mmol) in CH3CN (50 ml) was stirred under reflux and the reaction was followed by HPLC. After complete reaction (36 to 48 h) the mixture was cooled to 20-25° C., water (50 ml) was added and the suspension was stirred for 3 h. The product was filtered off, washed with water (2×25 ml) and dried to constant weight under vacuum and a slight stream of N2 at 50° C. Yield: 5.5 g (87% abs.). Assay (HPLC): 97% pure vs. standard.

Workup

stirringwas stirred
temperatureunder reflux
customAfter complete reaction (36 to 48 h) the mixture
stirringthe suspension was stirred for 3 h
filtrationThe product was filtered off
washwashed with water (2×25 ml)
customdried to constant weight under vacuum
customat 50° C

Sources & evidence

ORD record: ord-2d906ba5a0414d8493a35b42bf5ff409
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459556B2

Reaction notes

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