Sodium borohydride → HCID 67684370, compound

HRID 342215Notes

Reaction equation

[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)=[N:18][CH2:17][CH2:16]2)[CH3:5])[CH:2]=[CH2:3].[BH4-].[Na+]>C(O)C>[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([C:23]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=1)[NH:18][CH2:17][CH2:16]2)[CH3:5])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

0.3 g of allyl-[6-[1-(4-bromo-phenyl)-3,4-dihydro-isoquinolin-6-yloxy]-hexyl]-methyl-amine (Ex. 20d) is dissolved in 50 ml of ethanol and cooled to 0° C. using an ice bath. A total of 0.185 g of sodium borohydride is added in three portions within 10 minutes and the mixture is warmed to room temperature and stirred overnight. For the working-up, the reaction mixture is evaporated to a quarter and adjusted to pH~2 with 2M hydrochloric acid solution, again made basic with concentrated ammonia solution and extracted three times with methylene chloride. After evaporation of the organic extracts and chromatography of the residue on silica gel with toluene/acetone/triethylamine (50:49:1) as the eluent there is obtained 0.23 g of (RS)-allyl-[6-[1-(4-bromo-phenyl)-1,2,3,4-tetrahydro-isoquinolin-6-yloxy]-hexyl]-methyl-amine which is converted into the hydrochloride, MS: m/e 457 (M+H+, 1 Br).

Workup

temperaturethe mixture is warmed to room temperature
customthe reaction mixture is evaporated to a quarter
extractionextracted three times with methylene chloride
customAfter evaporation of the organic extracts and chromatography of the residue on silica gel with toluene/acetone/triethylamine (50:49:1) as the eluent there

Sources & evidence

ORD record: ord-65308e65cef14f7eb4aca96f25208c38
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856503

Reaction notes

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