Water → HCID 54508834, compound

HRID 2248125Notes

Reaction equation

[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:19])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([NH:14]3)[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1.[CH:20](N(C(C)C)CC)([CH3:22])[CH3:21].C(Br)C=C.O>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH2:3][N:4]=[CH:5][C:6]2([CH3:19])[CH:17]([CH3:18])[CH:15]3[CH2:16][C:10]4=[C:11]([N:14]3[CH2:22][CH:20]=[CH2:21])[CH2:12][CH2:13][C:7]2=[C:8]4[CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1.30 g of 10-chloro-6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]-benzazocine, and 24 ml of dimethylformamide was added 1.69 ml of diisopropylethyl amine. Upon cooling to 0° C., the mixture was cooled to 0° C. and 0.45 ml of allyl bromide in 5.0 ml of dimethylformamide was added, under nitrogen. The mixture was stirred an additional 3 hr at 0° C. and was poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and concentrated. The residue crystallized on standing. Recrystallization from ether with ether-pentane and pentane washing gave 0.75 g (47%) of product, mp 189°-191° C.

Workup

temperaturethe mixture was cooled to 0° C.
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate and ether
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous potassium carbonate
filtrationfiltered
concentrationconcentrated
customThe residue crystallized
customRecrystallization from ether with ether-pentane and pentane washing

Sources & evidence

ORD record: ord-67547fc3c7644c6cad8fbf171739569f
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05037985

Reaction notes

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