Hydrogen Bromide → HCID 23625665, compound

HRID 733484Notes

Reaction equation

HRID 733484 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:24][CH3:25])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])C1C=CC=CC=1.Br.[OH-].[Na+]>CC(O)=O.O>[CH2:24]([N:14]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH2:13][CH2:12][CH2:11][NH2:10])[CH3:25]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 23625344HCID 23625344, compound

Product 1

HCID 23625665HCID 23625665, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of {3-[ethyl-(2-methoxy-benzyl)-amino]-propyl}-carbamic benzyl ester acid (1.4 g; 3.9 mmol) in 15 ml of glacial CH3COOH, 3.5 ml of a 33% solution of HBr in CH3COOH was added cautiously. It was left in agitation for 2 h, then the hydrobromate was precipitated with 100 ml of diethyl ether. The white solid formed was solubilised in H2O, basified with NaOH 2N and extracted with CHCl3 (5×20 ml). The anhydrified organic phase was evaporated in a vacuum to give 0.87 g of the compound XI as pure transparent oil on TLC (eluant CHCl3/MeOH/NH4OH 9.0:1.0:0.1); quantity yield; 1H NMR (free base; CDCl3) δ: 1.07 (t, 3H), 1.50 (s enlarged, 2H exchangeable with D2O), 1.57-1.71 (m, 2H), 2.55 (q, 4H), 2.73 (t, 2H), 3.60 (s, 2H), 3.84 (s, 3H), 6.83-6.99 (m, 2H), 7.19-7.44 (m, 2H).

Workup

  1. customthe hydrobromate was precipitated with 100 ml of diethyl ether
  2. customThe white solid formed
  3. extractionextracted with CHCl3 (5×20 ml)
  4. customThe anhydrified organic phase was evaporated in a vacuum

Sources & evidence

ORD record
ord-5d34445e68ca479785c4b55e82c2689f
Source dataset
uspto-grants-2009_09
Patent number
US07589219B2

Reaction notes

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