Hydrochloric Acid → 4H-1,3-Benzodioxin-2-methanamine, 6-chloro-N-(1-methylethyl)-4-phenyl-, hydrochloride, cis-

HRID 1438731Notes

Reaction equation

HRID 1438731 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C@H:7]([C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=O)[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.B#B.Cl>C1COCC1.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C@H:7]([CH2:16][NH:18][CH:19]([CH3:20])[CH3:21])[O:8][C@H:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6328200DiboronHCID 22799976HCID 22799976, compound

Product 1

HCID 30497024H-1,3-Benzodioxin-2-methanamine, 6-chloro-N-(1-methylethyl)-4-phenyl-, hydrochloride, cis-Yield 208.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of cis-6-chloro-4-phenyl-N-(2-propyl)-1,3-benzodioxan-2-carboxamide (6.6 g, 20.0 mmoles) in 400 ml of anhydrous THF was treated with 80 ml (80 mmoles) of diborane in THF solution (1M as BH3) and the reaction mixture was worked up essentially as described in Example 5b. The oily amine was converted to the hydrochloride in anhydrous ether; 7.4 g of colorless powder was obtained. Recrystallization from absolute EtOH gave 5.96 g (84%) of colorless crystals; mp 224.5°-225.5°.

Sources & evidence

ORD record
ord-c8f9a85b3d4345dcac53b00d1d28eb9f
Source dataset
uspto-grants-1977_11
Patent number
US04056540

Reaction notes

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