Phosphorus tribromide → HCID 18607407, compound

HRID 542933Notes

Reaction equation

O=[C:2]1[NH:17][C:5]2[CH2:6][C@H:7]3[C@H:12]([CH2:13][C:4]=2[O:3]1)[N:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9][CH2:8]3.P(Cl)(Cl)(Cl)(Cl)[Cl:19].P(Cl)(Cl)(Cl)=O.P(Br)(Br)[Br:30]>>[Cl:19][C:2]1[O:3][C:4]2[CH2:13][C@H:12]3[C@@H:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=2[N:17]=1.[Br:30][C:2]1[O:3][C:4]2[CH2:13][C@H:12]3[C@@H:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=2[N:17]=1

Participants

Reactant 4

HCID 24614Phosphorus tribromide

HCID 24813Phosphorus oxychloride

HCID 24819Phosphorus pentachloride

HCID 18607411HCID 18607411, compound

Product 2

HCID 18607407HCID 18607407, compound

HCID 18607408HCID 18607408, compound

Procedure

Trans-(±)-2-oxo-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydro-1H-oxazolo[4,5-g]quinoline thus prepared can be reacted with phosphorous pentachloride or phosphorous oxychloride or PBr3 to yield the corresponding chloro or bromo derivative, trans-(±)-2-chloro-5-n-propyl-4,4a,5,6,7,8,8a,9-octa hydro-oxazolo[4,5-g]quinoline or trans-(±)-2-bromo-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydro-oxazolo[4,5-g]quinoline. This compound can in turn be reacted with secondary or primary amines with ammonia or with cyclic amines such as piperidine, pyrrolidine or morpholine to yield the corresponding 2-amino or substituted amino octahydro-oxazolo[4,5-g]quinoline.

Sources & evidence

ORD record: ord-2f92a43a62e242f6ba9466969c557b1a
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659832

Reaction notes

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