Water → N,N-Dimethyl-N-[4-(3-methyl-1H-pyrrolo[3.2-c]pyridin-2-yl)-1-phenylcyclohex-3-enyl]amine

HRID 1095592Notes

Reaction equation

O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][N:16]([CH3:40])[C:17]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:22][CH2:21][C:20]([C:24]2[NH:32][C:31]3[CH:30]=[CH:29][N:28]=[CH:27][C:26]=3[C:25]=2[CH3:33])(O)[CH2:19][CH2:18]1.O.[OH-].[Na+]>CS(O)(=O)=O.C(Cl)Cl>[CH3:40][N:16]([CH3:15])[C:17]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:22][CH2:21][C:20]([C:24]2[NH:32][C:31]3[CH:30]=[CH:29][N:28]=[CH:27][C:26]=3[C:25]=2[CH3:33])=[CH:19][CH2:18]1

Participants

Conditions

Temperature: 77 °C

Procedure

P4O10 (approx. 1 g, two spatula-tips) was added to a solution of 4-dimethylamino-1-(3-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-4-phenylcyclohexanol (600 mg, 1.72 mmol) in methanesulfonic acid (20 ml). The slightly pale brown-coloured solution was stirred at 77° C. (oil bath temperature) for 3 h. Water (10 ml) was added to the reaction mixture and this was rendered basic with sodium hydroxide solution (5 M). Methylene chloride (30 ml) was then added and the mixture was stirred for 10 min. The phases were separated. The aqueous phase was extracted with methylene chloride (3×35 ml). The combined organic phases were dried over sodium sulfate. The volatile constituents were then removed completely in vacuo. 425 mg of (±)-N,N-dimethyl-N-[4-(3-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1-phenylcyclohex-3-enyl]amine remained (dark brown solid, slightly contaminated).

Workup

stirringthe mixture was stirred for 10 min
customThe phases were separated
extractionThe aqueous phase was extracted with methylene chloride (3×35 ml)
dry with materialThe combined organic phases were dried over sodium sulfate
customThe volatile constituents were then removed completely in vacuo

Sources & evidence

ORD record: ord-83cbb9acfa9e4373af87e7e5f63cc739
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138187B2

Reaction notes

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