Hydrochloric Acid → 4-(1-Amino-1-phenyl-ethyl)-cyclohexanol

HRID 45204Notes

Reaction equation

HRID 45204 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]([CH:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])(C)(C)C.Cl.O>ClCCl.C(#N)C>[NH2:14][C:15]([CH:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6422Trifluoroacetic acidHCID 70252586[1-(4-Hydroxy-cyclohexyl)-1-phenyl-ethyl]carbamic acid tert-butyl ester

Product 1

HCID 583809984-(1-Amino-1-phenyl-ethyl)-cyclohexanol

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8 mL) was added to a solution of [1-(4-hydroxy-cyclohexyl)-1-phenyl-ethyl]-carbamic acid tert-butyl ester (29) in dichloromethane (75 mL) from the previous stage. After stirring for 4 hours the reaction mixture was worked up by adding 2M aqueous hydrochloric acid (39 mL), followed by evaporation. Freeze drying overnight gave a pale brown semi-solid residue. This was treated with a mixture of water and acetonitrile. After freeze drying again 1.24 g of crude product as the hydrochloride was obtained which was used in the next stage without further purification. Rt=0.58 min (Method 5). Detected mass: 185.15 (M—NH3—H2O+H+).

Workup

  1. customfollowed by evaporation
  2. customFreeze drying overnight
  3. customgave a pale brown semi-solid residue
  4. dry with materialAfter freeze drying again 1.24 g of crude product as the hydrochloride
  5. customwas obtained which
  6. customwas used in the next stage without further purification

Sources & evidence

ORD record
ord-1b63e111a78a4302b33a44161cc912ac
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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