Water → HCID 54508834, compound

HRID 1885744Notes

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-e329edcc99d64fce8c4eba5a7b41cf50
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145965

Reaction notes

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