Hydrochloric Acid → HCID 11200850, compound

HRID 1525612Notes

Reaction equation

[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[C:5](=O)[CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[BH4-].[Na+].B(F)(F)F.CCOCC.Cl>O.O1CCCC1>[CH:30]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 2 °C

Procedure

N,N-diisopropyl-3-(2-benzyloxy-5-methyl-phenyl)-3-phenyl propane amide (1.0 Kg,), Tetrahydrofuran (5.0 lit) and Sodium borohydride (0.43 Kg) were taken into the round bottom flask. The contents were cooled to 2±3° C. followed by drop wise addition of Borontrifluoride etherate (1.93 Kg). The reaction mixture was stirred for 10-12 hrs at 33±2° C. After completion of the reaction a solution of Conc. Hydrochloric acid (2.83 L) into Process water (2.83 L) was added to the reaction mass at 40±10° C. and stirred for 2-3 hrs at 62±3° C. The product was extracted in dichloromethane (4.0 L). Dichloromethane distilled out completely under vacuum below 50° C. This was followed by addition of Isopropyl alcohol (1.0 L) and distilled it completely to give (±) N,N-diisopropyl-3-(2-benzyloxy-5-methylphenyl)-3-phenyl propane amine.

Workup

additionwas added to the reaction mass at 40±10° C.
stirringstirred for 2-3 hrs at 62±3° C
extractionThe product was extracted in dichloromethane (4.0 L)
distillationDichloromethane distilled out completely under vacuum below 50° C
additionThis was followed by addition of Isopropyl alcohol (1.0 L)
distillationdistilled it completely

Sources & evidence

ORD record: ord-6aefd84bc5e543b99e44dcf8f1dee18a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085509B2

Reaction notes

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