Water → HCID 66991117, compound

HRID 557505Notes

Reaction equation

HRID 557505 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[C:8]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:7](C)[CH:6]=[CH:5][C:4]=1O.[OH2:18].[CH3:19][Si](C)(C)[Cl:21]>C(C(C)=O)C>[ClH:21].[CH3:17][N:2]([CH3:1])[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([CH3:19])[C:9]1[CH:10]=[C:11]([OH:18])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 86623799HCID 86623799, compound

Product 1

HCID 66991117HCID 66991117, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

In order to prepare the hydrochloride salt, 42 g of the base 3-[2-(dimethylamino)methyl(cyclohex-1-yl)phenol were added to 210 ml methyl ethyl ketone. Subsequently 2 ml water and 23 ml trimethylchlorosilane, dissolved in 45 ml methyl ethyl ketone, were added. The reaction mixture was cooled down to 0° C. by cooling with ice and was kept cold overnight (in a refrigerator at about 4° C.). The solid substance that precipitated out was filtered out by suction using a suction filter, with application of a vacuum, and then washed with 30 ml of acetone. The yield of 3-[2-(dimethylamino)methyl(cyclohex-1-yl)]phenol hydrochloride was 49 g (corresponding to 100% of the theoretical value). According to NMR and GC analyses, the produce was >95% trans diastereomer. The melting-point was 122-126° C.

Workup

  1. additionwere added
  2. temperatureby cooling with ice
  3. customat about 4° C.
  4. customThe solid substance that precipitated out
  5. filtrationwas filtered out by suction
  6. filtrationfilter, with application of a vacuum
  7. washwashed with 30 ml of acetone
  8. custommelting-point was 122-126° C.

Sources & evidence

ORD record
ord-3ea91a682f484f74a2da12a41961fdf1
Source dataset
uspto-grants-2011_11
Patent number
US08058476B2

Reaction notes

Loading…