Hydrochloric Acid → Hydrochloric Acid

HRID 1379629Notes

Reaction equation

HRID 1379629 reaction equation
C(OC([NH:8][C@H:9]([CH3:18])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:19]>C(OCC)(=O)C>[O:11]([CH2:10][C@H:9]([NH2:8])[CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[ClH:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10586857(R)-N-Boc-1-phenoxy-2-propanamine

Product 2

HCID 313Hydrochloric AcidYield 69%HCID 5324633(2R)-1-Phenoxy-2-propanamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)- N-(tert-Butoxycarbonyl)-1-phenoxy-2-propylamine (8.0 g, 33 mmol) was dissolved in ethyl acetate (100 ml). A solution of hydrochloric acid (g) in ethyl acetate (6N, 100 ml) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 20 h during which time a heavy precipitate was formed. The reaction mixture was concentrated to half the original volume before the product was collected by filtration and dried in vacuo to provide the title compound as a white solid hydrochloride (4,3 g, 69%) m.p. 186°-189° C. 1H NMR (DMSO-d6)δ 1.31 (3H, d, --CH3), 3.51-3.60 (1H, m, --CH--), 4.05 (1H, dd, --CH2 a-), 4.12 (1H, dd, --CH2 b-), 6.95-7.00 (3H, m. Ar--H), 7.32 (2H, t, Ar--H).

Workup

  1. customwas formed
  2. concentrationThe reaction mixture was concentrated to half the original volume before the product
  3. filtrationwas collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6a4de2790c414dfc9e37f1da5f881710
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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