Ammonia methanol → HCID 57608401, compound

HRID 2098562Notes

Reaction equation

HRID 2098562 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[OH:23])[CH:10]=1)=O.N.CO>ClCCl>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]#[C:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[OH:23])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21705897Ammonia methanolHCID 86628457HCID 86628457, compound

Product 1

HCID 57608401HCID 57608401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deprotection of 2,2,2-trifluoro-N-(3-(3-((2-hydroxycyclohexyl)ethynyl)phenyl)propyl)acetamide followed by flash chromatography (10% (7N NH3/MeOH)/dichloromethane) gave 2-((3-(3-aminopropyl)phenyl)ethynyl)cyclohexanol as an orange oil. Yield (0.606 g, 69%): 1H NMR (400 MHz, CDCl3) δ 7.16-7.26 (m, 3H), 7.08-7.12 (m, 1H), 3.48-3.56 (m, 1H), 2.71 (t, J=7.2 Hz, 2H), 2.61 (t, J=7.2 Hz, 2H), 2.38-2.46 (m, 1H), 2.01-2.10 (m, 2H), 1.64-1.82 (m, 7H), 1.40-1.52 (m, 1H), 1.16-1.40 (m, 3H).

Sources & evidence

ORD record
ord-6cdf95db6d404968b4ed6efe464f81de
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

Loading…