Ammonia → Hydrochloric Acid

HRID 1704631Notes

Reaction equation

HRID 1704631 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:12])[CH2:8][C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.N.[Li].[Cl-:15].[NH4+]>O.C(O)(C)(C)C.O1CCCC1>[ClH:15].[ClH:15].[NH2:12][CH:7]([C:4]1[CH2:5][CH:6]=[CH:1][CH2:2][CH:3]=1)[CH2:8][C:9]([OH:11])=[O:10]

Participants

9

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 69189DL-beta-PhenylalanineHCID 3028194Lithium

Product 2

HCID 313Hydrochloric AcidHCID 70614091HCID 70614091, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of DL-β-amino-β-phenyl propionic acid (16.3 g) in liquid ammonia (800 ml.), tetrahydrofuran (200 ml.) and tertiary butanol (200 ml.) contained in a vacuum jacketed vessel, was added strips of lithium (8.0 g) over a period of 4 hours when a permanent blue colour was obtained. Ammonium chloride (62 g) was cautiously added and the ammonia allowed to slowly evaporate overnight. The white residue was dissolved in water (200 ml.), the volume reduced to about 50 ml. and the pH adjusted to 5.5. The white solid was collected and recrystallised from 5N. hydrochloric acid to give β-amino-β-cyclohex-1, 4-dienyl propionic acid hydrochloride [(15.0 g m.p. 210°-212°: (found C, 52.8; H, 7.0; N, 6.8; C9H14ClNO2 requires C, 53.1; H, 6.9; N, 6.8%) n.m.r. δp.p.m. [(CD3)SO] 9.0 (3H, m); 5.85 (H, s); 5.7 (2H, s)- 3.85 (H, t); 2.7 (6H, m) i.r. γmax (mull) 2600 and 1950 (NH+), 1730 (CO), 1600 cm-1 (C = C)].

Workup

  1. customwas obtained
  2. customThe white solid was collected
  3. customrecrystallised from 5N

Sources & evidence

ORD record
ord-ffea2f6a14384d15ac22407fd36cec08
Source dataset
uspto-grants-1978_11
Patent number
US04127570

Reaction notes

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