Phosphorus oxide (P4O10) → 4,4-Dimethyl-1-phenyl-3,4-dihydroisoquinoline

HRID 383992Notes

Reaction equation

O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O=P(Cl)(Cl)Cl.[CH3:20][C:21]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:32])[CH2:22][NH:23][C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1(C)C(C)=CC=CC=1>[CH3:20][C:21]1([CH3:32])[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:23][CH2:22]1

Participants

Conditions

Temperature: 150 °C

Procedure

1.42 g (10.0 mmol) of P2O5 and POCl3 (4 ml) were added to a solution of 1.27 g (5.0 mmol) of N-(2-methyl-2-phenylpropyl)benzamide in xylene (20 ml) and the mixture was heated at 150° C. for 3 h. After cooling to RT the mixture was concentrated to small volume under vacuum. The residue was made alkaline with a 20% aqueous NaOH solution. It was then extracted with EE and the organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. 634 mg (2.7 mmol) of 4,4-dimethyl-1-phenyl-3,4-dihydroisoquinoline were obtained as the residue, which was reacted further with no additional purification.

Workup

temperatureAfter cooling to RT the mixture
concentrationwas concentrated to small volume under vacuum
extractionIt was then extracted with EE
dry with materialthe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record: ord-cf2ff0bc9d5c444390e85e48dcfe4d1d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367700B2

Reaction notes

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