Hydrochloric Acid → (R)-N,N-Diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine hydrochloride

HRID 428316Notes

Reaction equation

HRID 428316 reaction equation
[ClH:1].[CH:2]([N:5]([CH:24]([CH3:26])[CH3:25])[CH2:6][CH2:7][C@@H:8]([C:15]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:16]=1[OH:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])[CH3:3]>C(OCC)C.CC(O)C.CO>[ClH:1].[CH:24]([N:5]([CH:2]([CH3:4])[CH3:3])[CH2:6][CH2:7][C@@H:8]([C:15]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:16]=1[OH:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 53380832(R)-N,N-diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine

Product 1

HCID 86757571(R)-N,N-Diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 3776IsopropanolSolvent

Procedure

Hydrogen chloride in diethyl ether was added to a solution of (R)-N,N-diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine (0.81 g, 2.4 mmol) in diethyl ether and 2-propanol. Crystals were filtered to yield 0.4 g (45%); mp 178-179° C. [α]Hg=−40° (c 1.1 in methanol). 1H NMR (DMSO-d6) δ1.16 (d, 3H), 1.20 (d, 3H), 1.24 (d, 3H), 1.27 (d, 3H), 2.54 (m, 2H), 2.84 (m, 1H), 2.97 (m, 1H), 3.58 (br, 2H), 4.38 (t, 1H), 7.08 (d, 1H), 7.22 (t, 1H), 7.32 (m,4H), 7.65 (dd, 1H), 7.83 (d, 1H), 9.80 (s, 1H), 9.86 (br, 1H) 10.99 (s, 1H). Anal. (C22H29NO2.HCl) H, N; C: calcd, 70.3; found, 70.8.

Workup

  1. filtrationCrystals were filtered
  2. customto yield 0.4 g (45%)

Sources & evidence

ORD record
ord-4a224bd842994cf2afc75fcf89ba456b
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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